Pesticidal compounds

ABSTRACT

The present invention relates to the compounds of formula (I), and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein the variables are defined according to the description, (I) The compounds of formula (I), as well as the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

Invertebrate pests and in particular insects, arachnids and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby causing large economic loss to the food supply and to property. Accordingly, there is an ongoing need for new agents for combating invertebrate pests.

Carbamoylated and thiocarbamoylated oxime derivatives are known for pesticidal use, for example, in patent publications WO 2016/156076, semi-carbazones and thiosemicarbazones derivatives are known for pesticidal use in patent publication WO 2016/116445.

Due to the ability of target pests to develop resistance to pesticidally-active agents, there is an ongoing need to identify further compounds, which are suitable for combating invertebrate pests such as insects, arachnids and nematodes. Furthermore, there is a need for new compounds having a high pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control insects, arachnids and nematodes.

It is therefore an object of the present invention to identify and provide compounds, which exhibit a high pesticidal activity and have a broad activity spectrum against invertebrate pests.

It has been found that these objects can be achieved by substituted bicyclic compounds of formula I, as depicted and defined below, including their stereoisomers, their salts, in particular their agriculturally or veterinarily acceptable salts, their tautomers and their N-oxides.

In a first aspect, the present invention relates to the compounds of formula I,

wherein

-   A is N or CR^(A); -   B¹ is N or CR^(B1); -   B² is N or CR^(B2); -   B³ is N or CR^(B3); -   B⁴ is N or CR^(B4); -   W is O, S(═O)_(m), or NR⁶; -   R^(A) is H, halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl,     C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,     C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,     C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,     C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl,     alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or     substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c),     C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c),     C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c),     C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy,     phenylcarbonyl, phenylthio, or —CH₂-phenyl, wherein the phenyl rings     are unsubstituted or substituted with R^(f); -   R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are     H, halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy,     C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,     C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,     C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,     C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl,     alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or     substituted with halogen, -   C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),     O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,     NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d),     SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy, phenylcarbonyl,     phenylthio, or —CH₂-phenyl, wherein the phenyl rings are     unsubstituted or substituted with R^(f); -   Q is —C(R⁴R⁵)—O—, —C(═O)—O—, —S(═O)_(m)—C(R⁷R⁸)—, —N(R²)—S(═O)_(m)—,     —N(R²)—C(R⁹R¹⁰)—, —C(═O)—C(R¹⁹R²⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═S)—,     —C(R¹³R¹⁴)—C(R¹⁵R¹⁶)—, —N═C(X)—, or —N(R²)—C(═NR)—; wherein Ar is     bound to either side of Q; -   m is 0, 1, or 2; -   X is H, halogen, SR⁷, OR⁸, or N(R³)₂; -   R is H, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, or     C₃-C₆-cycloalkyl, wherein the alkyl, alkenyl, and cycloalkyl     moieties are unsubstituted or substituted with halogen, OR⁸, N(R³)₂; -   R³ is H, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl; -   R² is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,     C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,     C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein     the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy     moieties are unsubstituted or substituted with halogen,     -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,         C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e),         phenyl, or —CH₂-phenyl, wherein the phenyl rings are         unsubstituted or substituted with R^(f); -   R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁹, R²⁰ are, identical     or different, H, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,     C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,     C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein     the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy     moieties are unsubstituted or substituted with halogen,     -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,         C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e),         phenyl, or —CH₂-phenyl, wherein the phenyl rings are         unsubstituted or substituted with R^(f); -   R⁶ is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,     C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,     C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein     the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy     moieties are unsubstituted or substituted with halogen,     -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,         C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e),         phenyl, —CH₂—C(═O)—OR^(a), or —CH₂-phenyl, wherein the phenyl         rings are unsubstituted or substituted with R^(f); -   Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or     substituted with R^(Ar), wherein     -   R^(Ar) is halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,         C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl,         wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and         cycloalkoxy moieties are unsubstituted or substituted with         halogen,         -   C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),             O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,             NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c),             C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl,             phenoxy, phenylcarbonyl, phenylthio or —CH₂-phenyl, wherein             phenyl rings are unsubstituted or substituted with R^(f); -   R¹ is a moiety of formula Y—Z-T-R¹¹ or Y—Z-T-R¹²; wherein     -   Y is —CR^(ya)═N—, wherein the N is bound to Z;         -   —NR^(yc)—C(═O)—, wherein C(═O) is bound to Z; or         -   —NR^(yc)—C(═S)—, wherein C(═S) is bound to Z;     -   Z is a single bond;         -   —NR^(zc)—C(═O)—, wherein C(═O) is bound to T;         -   —NR^(zc)—C(═S)—, wherein C(═S) is bound to T;         -   —N═C(S—R^(za))—, wherein T is bound to the carbon atom;         -   —O—C(═O)—, wherein T is bound to the carbon atom; or         -   —NR^(zc)—C(S—R^(za))═, wherein T is bound to the carbon             atom;         -   wherein if Y is other than —CR^(ya)═N—, Z is other than             —N═C(S—R^(za))—;     -   T is O, N or N—R^(T);     -   R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy,         wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and         cycloalkoxy moieties are unsubstituted or substituted with         halogen,         -   C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,             C(═O)—NR^(b)R^(c), C(═O)—R^(d), aryl, aryl-carbonyl,             aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl, hetaryl,             carbonyl-hetaryl, hetaryl-C₁-C₄-alkyl or             hetaryloxy-C₁-C₄-alkyl, wherein the phenyl rings are             unsubstituted or substituted with R^(g) and wherein the             hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9-             or 10-membered bicyclic hetaryl;     -   R¹² is a radical of the formula A¹;

-   -   wherein # indicates the point of attachment to T;         -   R¹²¹, R¹²², R¹²³ are, identical or different, H, halogen,             C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,             C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,             C₂-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₄-alkoxy,             C₁-C₆-alkylcarbonlyoxy, C₁-C₆-alkenylcarbonlyoxy,             C₃-C₆-cycloalkylcarbonlyoxy, wherein the alkyl, alkoxy,             alkenyl, alkenyloxy, alkynyl, alkynyloxy and cycloalkyl             moieties are unsubstituted or substituted with halogen, or             NR^(b)R^(c), or one of R¹²¹, R¹²², R¹²³ may also be oxo;         -   R¹²⁴ is H, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,             C₁-C₆-alkoxy, or C₂-C₆-alkenyloxy, wherein the alkyl,             alkoxy, alkenyl and alkenyloxy moieties are unsubstituted or             substituted with halogen;         -   and where     -   R^(ya) is H, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,         C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy,         wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and         cycloalkoxy moieties are unsubstituted or substituted with         halogen,         -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,             C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c),             S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl             rings are unsubstituted or substituted with R^(f);     -   R^(yc), R^(zc) are, identical or different, H, C₁-C₆-alkyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy,         C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl, or         C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy,         alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are         unsubstituted or substituted with halogen;     -   R^(T) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₄-alkyl-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl,         wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and         cycloalkoxy moieties are unsubstituted or substituted with         halogen,         -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,             C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c),             S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl             rings are unsubstituted or substituted with R^(f);     -   R^(zc) together with R^(T) if present, may form C₁-C₆-alkylene         or a linear C₂-C₆-alkenylene group, where in the linear         C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety may         be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂         moieties may be replaced by O or S and/or wherein the linear         C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be         unsubstituted or substituted with R^(h);     -   R^(za) is H, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,         tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy,         C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy,         C₁-C₄-alkyl-C₃-C₆-cycloalkyl, wherein the alkyl, alkoxy,         alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are         unsubstituted or substituted with halogen,         -   C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,             C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, phenylcarbonyl, or             —CH₂-phenyl, wherein the phenyl rings are unsubstituted or             substituted with R^(f);     -   R^(za) together with R^(T) if present, may form C₁-C₆-alkylene         or a linear C₂-C₆-alkenylene group, where in the linear         C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety may         be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂         moieties may be replaced by O or S and/or wherein the linear         C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be         unsubstituted or substituted with R^(h);     -   R^(a), R^(b) and R^(c) are, identical or different, H,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cyclo-alkoxy-C₁-C₄-alkyl,         wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and         cycloalkoxy moieties are unsubstituted or substituted with         halogen,         -   C₁-C₆-alkylene-CN, phenyl, or —CH₂-phenyl, wherein the             phenyl rings are unsubstituted or substituted with R^(f);     -   R^(d) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl,         wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and         cycloalkoxy moieties are un-substituted or substituted with         halogen,         -   phenyl, or —CH₂-phenyl, wherein the phenyl rings are             unsubstituted or substituted with R^(f);     -   R^(e) is C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₄-alkyl, wherein the alkyl, cycloalkyl         moieties are unsubstituted or substituted with halogen, phenyl         and —CH₂-phenyl, wherein the phenyl rings are unsubstituted or         substituted with R^(f);     -   R^(f) is halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,         C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxyx-C₁-C₄-alkyl,         wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and         cycloalkoxy moieties are unsubstituted or substituted with         halogen,         -   C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),             O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,             NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c),             C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e);     -   R^(g) is halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,         C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,         C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl,         wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and         cycloalkoxy moieties are unsubstituted or substituted with         halogen,         -   C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),             O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,             NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c),             C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e);     -   R^(h) is halogen, OH, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, or CN;         except the compound tert-Butyl         N-[4-(5-[3-(aminocarbonyl)-2,4-difluorophenoxy]methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamate;

-   and the N-oxides, stereoisomers, tautomers and agriculturally or     veterinarily acceptable salts thereof.

Moreover, the present invention also relates to processes and intermediates for preparing compounds of formula I and to active compound combinations comprising them. Moreover, the present invention relates to agricultural or veterinary compositions comprising the compounds of formula I, and to the use of the compounds of formula I or compositions comprising them for combating or controlling invertebrate pests and/or for protecting crops, plants, plant propagation material and/or growing plants from attack and/or infestation by invertebrate pests. The present invention also relates to methods of applying the compounds of formula I. Furthermore, the present invention relates to seed comprising compounds of formula I. Wherein the compounds of formula I includes N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

General Procedure:

With due modification of the starting compounds, the compounds of formula I can be prepared by procedures as given in below schemes.

General Procedure:

The compounds of the formula (I) can be prepared by methods of organic chemistry, e.g, by the methods described herein after in schemes 1 to 21 and in the synthesis description of the examples. In the schemes 1 to 21, the radicals Ar, A, B¹, B², B³, B⁴, Q and R¹, R², R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R^(ya), R^(zc), R^(yc), R^(yz), R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁹ and R²⁰ are as defined above for formula (1), unless otherwise specified.

Compounds of formula (I), wherein Z is a single bond or —NR^(zc)—C(═S)— or —NR^(zc)—C(═O) and T is O, N or N—R^(T), are the compounds of formula (Ia) and can be prepared by analogy to the methods described in WO 2011/017504 or WO 2015/007682 or methods described in Scheme 1.

In one embodiment of Scheme 1, an aldehyde or ketone of the formula (II) is reacted with a compound of formula (E1) wherein Z is —NR^(zc)—C(═S) or —NR^(zc)—C(═O) and T is N, in the presence or in the absence of a solvent. Suitable solvents are polar protic solvents. If the reaction is performed in the absence of a solvent, the compound of the formula (E1) usually also act as solvent. Compounds of the formula (E1) are commercially available or can be prepared using organic reactions analogy to method as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March.

According to another embodiment of Scheme 1, an aldehyde or ketone compound of the formula (II) is first reacted with a hydrazine of the formula R^(zc)NHNH₂ followed by the reaction with an isocyanate of the formula R¹¹—NCO or with an isothiocyanate R¹¹—NCS to yield a compound of the formula (Ia), wherein Z is —N(R^(zc))—C(═O) or —N(R^(zc))—C(═S) and T is N.

According to another embodiment of Scheme 1, an aldehyde or ketone compound of the formula (II) is first reacted with a hydroxylamine followed by the reaction with a compound R¹²—L, where L is a suitable leaving group, such as halogen or activated OH. Thereby, a compound of the formula (Ia) will result, wherein Z is a single bond and T is O.

According to another embodiment of the above reaction, an aldehyde or ketone compound of formula (II) is first reacted with a hydroxylamine followed by reaction with an isocyanate of the formula R¹¹—NCO or with an isothiocyanate R¹¹—NCS to yield a compound of the formula (Ia), wherein Z is —O—C(═O)— or —O—C(═S)— and T is N.

Compounds of formula (Ib) wherein Z is NR^(zc)C(═S) or NR^(zc)C(═O), wherein C(═S) or C(═O) is bound to T and T is O, N or N—R^(T), can be prepared by analogy to the method described in Synthesis, 2010, 2990-296 or as shown in Scheme 2.

According to the method depicted in scheme 2, an isocyanate compound of the formula (IIIa) is reacted with the compound of formula (E2) by methods of isocyanate chemistry. The isocyanate of the formula (IIIa) can be obtained e.g. via Lossen rearrangement of the corresponding hydroxamic acid (IVa). The hydroxamic acid (IVa) is reacted with 1-propanephosphonic acid cyclic anhydride (T3P) in the presence of a base. The base is preferably N-methylmorpholine. The isocyanate of the formula (IIIa) may also be obtained via Curtius rearrangement of the corresponding azide of the formula (IVb), e.g. by analogy to the method described in WO 2014/204622.

For converting compounds of formula (Ia) and (Ib) wherein R^(yz) or R^(zc) is H into compounds (I) wherein R^(yz) or R^(zc) is different from H, compounds of formula (Ia) and (Ib) wherein R^(yz) or R^(zc) is H can be reacted with compounds of formulae R^(yz)—Lg or R^(zc)—Lg wherein R^(yz) or R^(zc) is not H and Lg is a leaving group, such as a bromine, chlorine or iodine atom or a tosylate, mesylate or triflate, to yield compounds of formula (Ia) and (Ib), wherein R^(yz) or R^(zc) is different from H. The reaction is suitably carried out in the presence of a base such as sodium hydride or potassium hydride, suitably in a polar aprotic solvent such as N,N-dimethylformamide, tetrahydrofuran, dioxane, acetonitrile, dimethylsulfoxide or pyridine, or mixtures of these solvents, in a temperature range of from 0° C. and 100° C.

Compounds of the formula (Ic) can be prepared from compounds of formula (IIc) by the reactions shown below.

R^(11/12) corresponds to radicals R¹¹ or R¹² respectively. The reaction shown above can be performed by analogy to conventional methods of preparing carbamates. According to a first embodiment, the amine of the formula (IIc) is converted into either an isocyanate or p-nitrophenyl carbamate followed by treatment with an alcohol of the formula R¹¹—OH or R¹²—OH, respectively, in the presence of an organic or inorganic base. According to another embodiment, the compound of the formula (IIc) is reacted with a chloroformate of the formula R^(11/12)—O—C(═O)—Cl. The chloroformate is prepared from the alcohols R^(11/12)—OH by treatment with phosgene or triphosgene in the presence of a base, e.g. pyridine. Compounds of formula (Ic), wherein Z is —N(R^(zc))—C(═O)— or —N(R^(zc))—C(═S)— can be prepared by analogy to the methods described in WO 2013/009791 or by analogy to methods described in US 2012/0202687.

Compounds of formula (IIb) and (IIc) can be prepared from compounds of formula (IIa) by the reactions shown below.

Reaction step (i) can be performed by analogy to method described in WO 2015/051341. Reaction step (ii) can be performed by analogy to method described in E. J. Med. Chem., 2012, 49, 310-323. Compounds of the formula (IIc) [reaction step (iii) of the above reaction] can be prepared by reacting compounds of the formula (Ila) with ammonia or amines of the formula R^(yc)NH₂ in the presence of a metal catalyst or its salts, preferably copper or its salts as described in Chem. Commun., 2009, 3035-3037.

Compounds of formula (IId-3), (IId-4), (IId-5), (IId-6), (IId-7) and (IId-9), where Q is —N(R²)—C(═O)— or —NR²—C(R⁹R¹⁰)— or —N(R²)—C(═S)— or —O—C(═O)— —C(R⁴R⁵)—O— or —C(R⁷R⁸)—S— or and W is N(R⁶) and A is CH can be prepared by the reactions shown below.

Compounds of formula (IId-1) can be prepared from a suitable starting point 2,4 dioxo-4-aryl-butyric acid ethyl ester derivative (IId, commercially available) in two steps as described in Chem. Central Journal, 2016, 10, 40/1-40/6. Compounds of formula (IId-2) can be prepared from ester intermediate (IId-1) by hydrolysis with suitable base like LiOH, NaOH, as mentioned in WO 2011/050245. Common intermediate of formula (IId-3) can be prepared via amide formation by reacting the compounds of formula (IId-2) with Ar—NH₂ in presence of suitable coupling reagent like HATU and base like DIPEA. Compounds of formula (IId-5) can be prepared by reaction of compounds of formula (IId-3) with P₂S₅ or Lawesson's reagent as described by, for example, Strong et al, J. Med. Chem., 2017, 60, 5556-5585. Compounds of formula (IId-4) can be prepared from a common intermediate of formula (IId-3) via amide reduction with LAH as described in Tet. Lett., 2015, 56 (16), 2062-2066. Compounds of formula (IId-6) can be prepared from a common intermediate of formula (IId-2) via esterification by reacting the compound of formula (IId-2) with ArOH in presence of acid. Common intermediate of formula (IId-7) can be prepared from formula (IId-1) by reduction in presence of suitable reducing agents like LiAlH₄ or DIBAL-H. Common intermediate of formula (IId-8) can be prepared from formula (IId-7) via etherification reaction through Mitsunobu reaction condition. The compounds of formula (IId-9) can be prepared from compounds of formula (IId-6) via two steps sequence involving intermediate of compounds of formula (IId-8). and Hal′ is chlorine, bromine, iodine, tosylate, mesylate or triflate. Steps (vi), (vii), (viii), (ix-1), (ix-2) and (x-1), (x-2) can be performed analogous to process as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March.

Compounds of formula (IIe-1), (IIe-2), (IIe-3), (IIe-4), (IIe-5), (IIe-6), (IIf-1), (IIf-2), (IIf-3), (IIf-4), (IIf-5) and (IIf-6) where Q is —N(R²)—C(═O)— or —N(R²)—C(═S)— or —C(R⁴R⁵)—O— and W is O or S and A is CH can be prepared by the reactions shown below.

Compounds of formula (IIe-1) could be synthesized from a benzadehyde derivative (1) via an oxime derivative (2) in two steps as described in Tet. Lett., 2016, 57(7), 719-722. Compounds of formula (IIe-2), (IIe-3), (IIe-4), (IIe-5), (IIe-6) and (IIe-7) can be prepared from a common intermediate (IIe-1) as described in Scheme-5.

Compounds of formula (IIf-1) can be synthesized from an acetonitrile precursor (3) via cyano-oxime intermediate (4) as described in Eur., J. Med. Chem., 2017, 125, 527-584. Similarly, compounds of formula (IIf-2), (IIf-3), (IIf-4), (IIf-5), (IIf-6) and (IIf-7) can be prepared from a common intermediate (IIf-1) as described in Scheme-5.

Compounds of formula (IIg-1), (IIg-2) and (IIg-3) where Q is —N═C(X)—, X is Cl or F and W is N(R⁶) or S or O and A is CH can be prepared by the reactions shown below.

Compounds of formula (IIg-1) can be prepared using the method analogous to step (vi) of scheme 5. Compounds of formula (IIg-2) can be prepared using thionyl chloride as described in Angew. Chem. Int. Ed., 2014, 53, 9068-9071. Compounds of formula (IIg-3) can be prepared from compounds of formula (IIg-2) by a method described in Australian Journal of Chemistry, 1999, 52, 807-811.

Compounds of formula (IIg-4), (IIg-5), (IIg-6) and (IIg-7) where Q is N═C(X)—, X is OR⁸ or SR⁷ or N(R³)₂ or NH₂CN and W is N(R⁶) and A is CH can be prepared by the reactions shown below.

Compounds of formula (IIg-4), (IIg-5), (IIg-6) and (IIg-7) can be prepared by heating compounds of formula (IIg-2) with compounds of the formula R⁸—OH or R⁷—SH or NH(R³)₂ or NH₂CN in a polar protic or aprotic solvents in an acidic, basic or neutral conditions as described in WO2010129053, WO2007146824 or Chem. Commun., 2014, 50, 1465.

Compounds of formula (IIh-1) and (IIh-4), where Q is —C(R¹⁹R²⁰)—C(═O)— or —C(═O)—C(R¹⁹R²⁰)— and W is N(R⁶) or O or S and A is CH can be prepared by the reactions shown below.

Compounds of formula (IIh-1) can be prepared from compounds of formula (IId-2) or (IIe-2) or (IIf-2) in two steps via intermediary of (IIg-8) and (IIg-9) as per methods described in Org. Lett., 2016, 18(23), 6026-6029. Compounds of formula (IIh-4) can be prepared starting from compounds of formula (IIg-8) in three steps via intermediary of (IIh-2) and (IIh-3). The first step (xvii-2) involve Arndt-Eistert homologation from (IIg-8) followed by Weinreb amide formation (step-xvii-3) and addition of an aryl Grignard reagent (step-xvii-4) as per methods described in Photochemical & Photobiological Sciences, 2014, 13(2), 324-341.

Compounds of formula (IIi-1) and (IIj-1) where Q is —NR²—C(R⁹R¹⁰) or —S(═O)_(m)—C(R⁷R⁸); W is O or S and A is CH can be prepared by the reactions shown below.

The compounds of formula (IIg-11) can be prepared from compounds of formula formula or (IIe-2) or (IIf-2) via two steps sequence involving intermediate of compounds of formula (IIg-10). Step (xviii) involves acid reduction to alcohol using LAH or BH₃-THF as reducing agent. Step (xix) involves oxidation of alcohol to aldehyde using Dess-Martin periodinane or Swern oxidation condition to afford the compounds of formula (IIg-11). Compounds of the formula (IIi-1) and (IIj-1) can be prepared from compounds of formula (IIg-12) by reacting with compounds of the formula Ar—NHR² or Ar—SH by heating in a polar protic or aprotic solvents in an acidic, basic or neutral conditions as described in WO 2010/129053, WO 2007/146824 or Chem. Commun., 2014, 50, 1465. Moreover, compounds of formula (IIj-1) can be further oxidised using mCPBA for preparing compounds with different oxidation states on sulphur, as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March. Compounds of formula (IIg-12) can be prepared from compounds of formula (IIg-10) using analogy to methods described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March.

Compounds of formula (III-1) and (III-2) where Q is —C(R¹³R¹⁴)—C(R¹⁵R¹⁶)— and W is N(R⁶) or O or S and A is CH can be prepared as per below reactions.

Two compounds of formula (III-1) and (III-2) can be prepared from compounds of formula (IIg-11) by Wittig reactions (step-xxii) using phosphorous Wittig ylide and bases like ^(t)BuOK in THF, followed by hydrogenation process (step-xxiii) known in organic chemistry such as using hydrogen gas and a suitable metal catalyst as described in Marchs Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March.

Compounds of formula (IIm-2) and (IIm-6) where Q is —C(═O)—O— and W is N(R⁶) or O and A is CH can be prepared as per below reactions.

Compounds of formula (IIm-1) can be prepared from a commercially available beta keto ester derivative (5) by reacting it with substituted hydrazines (R⁶NHNH₂) in protic solvents like EtOH and irradiating in microwave as described in Bioorg. Med. Chem. Lett., 2007, 17(5), 1189-1192. Compounds of formula (IIm-2) can be prepared from (IIm-1) by esterification process analogous to as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March. Compounds of formula (IIm-6) can be prepared from a beta keto ester (5) in three steps involving through the intermediary of (IIm-4) and (IIp-5) as described in Science of Synthesis, 2002, 11,229-288.

Compounds of formula (IIn-1), (IIn-2), (IIk-1) and (IIk-3), where Q is —C(R⁴R⁵)—O— or —C(R⁷R⁸)—S(═O)_(m)— and W is N(R⁶) or O and A is CH can be prepared as per below reactions.

Compounds of the formula (IIn-1) can be prepared from compounds of formula (IIm-1) by reacting with compounds of the formula ArC(R⁴R⁵)-Lg (where Lg is bromine, chlorine, iodine, tosylate, or mesylate) with compounds of formula (IIm-1) in polar and aprotic solvents in presence of a base like NaH or K₂CO₃. Compounds of the formula (IIm-3) can be prepared from compounds of formula (IIm-1) by reacting with Lawesson's reagent as described in J. Med. Chem., 1992, 35(2), 368-374. Compounds of the formula (IIn-2) can be prepared from compounds of formula (IIm-3) by reacting with compounds of the formula ArC(R⁷R⁸)-Lg (where Lg is bromine, chlorine, iodine) in polar and aprotic solvents in presence of a base like NaH or K₂CO₃ etc. Compounds of formula (IIn-2) can be further oxidised using mCPBA for preparing compounds with different oxidation states on sulphur, as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March. Steps (xxvi-4), (xxvi-5) and (xxvi-6) are analogous to steps (xxvi-1), (xxvi-2) and (xxvi-3).

Compounds of formula (IIn-5), where Q is —N(R²)—S(═O)_(m)— and W is N(R⁶) or O and A is CH can be prepared as per below reactions.

Compounds of formula (IIn-5) can be prepared starting from compounds of formula (IIm-3) in three steps involving through the intermediary of (IIn-3) and (IIn-4) using the suitable reaction conditions as described in Chemistry Select, 2016, 3, 490-494, (step (xxvii-1), EP1992/524634 [step(xxvii-2)], Chemistry—A European Journal, 2014, 20(1), 317-322 (step-xxvii-3).

Compounds of formula (IIo), (IIo-1), (IIo-2), (IIo-3), (IIo-4), (IIo-6), (IIo-7), (IIo-9) and (IIo-12), where Q is —C(R⁹R¹⁰)—N(R²)— or —C(═O)—N(R²)— or —C(═S)—N(R²)— or —S(═O)_(m)—N(R²)— or —O—C(═O)— or —C(R⁴R⁵)—O— or —C(R⁷R⁸)—S(═O)_(m)— or —N(R²)—S(═O)_(m)— and W is S and A is CH can be prepared as per below reactions.

Compounds of formula (IIo-1), (IIo-2), (IIo-3) and (IIo-4) can be prepared from a common intermediate (IIo). The intermediate (IIo) can be synthesized from commercially available benzonitrile derivative (6) in two steps (steps xxviii and xxix) involving through an acetonitrile intermediate (7), as described Tet. Lett. 2015, 56, 2605-2607. Compounds of formula (IIo-1, IIo-2, IIo-3 and IIo-4) can be synthesized from compounds of formula (IIo) following known procedure (steps: xxx-1 , xxx-2, xxx-3 and xxx-4) as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March. Step (xxx-5) can be performed as described in Heteroatom Chemistry, 2015, 26(6), 411-416. Compounds of formula (IIo-6) and (IIo-7) can be synthesized from compounds of formula (IIo-5) following known procedure as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March. Compounds of formula (IIo-9) and (IIo-12) can be prepared by the method mentioned in scheme 13 and scheme 14.

Compounds of formula (IIp-1), (IIp-2), (IIp-3), (IIp-4) and (IIp-7), where Q is —C(R⁹R¹⁰)—N(R²)— or —C(═O)—N(R²)— —C(═S)—N(R²)— or —S(═O)_(m)—N(R²)— or —C(═O)—O— and W is N(R⁶) or O and A is CH can be prepared as per below reactions.

Compounds of formula (IIp) can be prepared from a suitably substituted and commercially available benzoyl acetonitrile derivative (7) by reacting it with substituted hydrazines under sealed tube condition (step-xxxi) as described in Org. Lett., 2017, 19 (4), 934-937. Compounds of formula (IIp-1) can be prepared by heating compounds of the formula Ar—C(R⁹R¹⁰)-Lg (where Lg is bromine, chlorine, tosylate, or mesylate with compounds of formula (IIp) in a polar protic or aprotic solvents in an acidic, basic or neutral conditions as described in WO 2010/129053, WO 2007/146824 or Chem. Commun., 2014, 50, 1465, shown in step (xxxii-1). Compounds of formula (IIp-2)can be prepared from compounds of formula (IIp) by using amide coupling reactions analogous to as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March, shown in step (xxxii-3). Compounds of formula (IIp-3) can be prepared by reaction of compounds of formula (IIp-2) with P₂S₅ or Lawesson's reagent as described by, for example, Strong. et al, J. Med. Chem., 2017, 60, 5556-5585 as shown in step (xxxii-3). Compounds of formula (IIp-4) can be prepared from compounds of formula (IIp) by treating with suitable Ar—SO₃Cl in presence of bases like pyridine and coupling reagents like DMAP, as described in Chemistry—A European Journal, 2014, 20(1), 317-322 (step-xxxii-4).

Compounds of formula (IIq-1) and IIq-2), where W is N(R⁶) and A is N can be prepared as per below reactions.

Compounds of formula (IIg-1) and (IIg-2) can be prepared from commercially available a benzoic acid derivative (8) through intermediary of compounds of formula (9) and (IIg-1) in three steps (steps-xxxiii-1, xxxiii-2 and xxxiii-3) as described in Eur. J. of Med. Chem., 2016, 113, 11-27.

Compounds of formula (IIr-1) and (IIs-1), where W is O or S and A is N can be prepared as per below reactions.

Compounds of formula (IIr-1) can be prepared from commercially available benzonitrile derivative (10) in two steps (xxxiv and xxxv) via an intermediate (11), as described in Zeitschrift fuer Chemie, 1975, 15(2), 57. Similarly, compounds of formula (115-1) can be prepared from commercially available starting materials like a phenyl boronic acid (12) and a thiadiazole halide under the Suzuki cross coupling reaction (step-xxxvi) condition as described in Org. Lett., 2009, 11(24), 5666-5669.

Compounds of formula (IIt-1), (IIt-2) and (IIt-3), where Q is —C(R⁹R¹⁰)—N(R²)— or —C(═O)—N(R²)— or C(═S)—N(R²)— or —S(═O)_(m)—N(R²)— and W is N(R⁶) or O or S and A is N can be prepared as per below reactions.

Compounds of formula (IIt-1) can be prepared by heating compounds of the formula Ar—C(R⁹R¹⁰)-Lg (where Lg can be bromine, chlorine, tosylate, mesylate) with the common intermediate of compounds of formula (IIt) in a polar protic or aprotic solvents in an acidic, basic or neutral conditions analogous to as described in WO 2010/129053, WO 2007/0146824 or Chem. Comnun., 2014, 50, 1465, shown in step (xxxvii-1). Compounds of formula (IIt-2) can be prepared from compounds of formula (IIt) by treating with suitable Ar—SO₂Cl in presence of bases like pyridine and coupling reagents like DMAP, as described in Chemistry—A European Journal, 2014, 20(1), 317-322, (step-xxxvii-2). Compounds of formula (IIt-3) can be prepared from compounds of formula (IIt) by using amide coupling reactions analogous to as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March, shown in step (xxxvii-3). Compounds of formula (IIt-4) can be prepared by reaction of compounds of formula (IIt-3) with P2S5 or Lawesson's reagent as described by, for example, Strong. et al, J. Med. Chem., 2017, 60, 5556-5585 as shown in step (xxxvii-4).

Compounds of formula (IIu-1) and (IIu-2), where Q is —N═C(X)—, X is Cl or F and W is O or S or N(R⁶) and A is N or CH can be prepared by the reactions shown below.

In the above reactions compounds of formula (IIu-1) can be prepared from compounds of formula (11t-3) using thionyl chloride as described in Angew. Chem. Int. Ed., 2014, 53, 9068-9071. Compounds of formula (IIu-2) can be prepared from compounds of formula (IIu-1) by a method described in Aust. J. Chem., 1999, 52, 807-811.

Compounds of formula (IIu-3), (IIu-4), (IIu-5) and (IIu-6), where Q is —C(X)═N—, X is OR⁸ or SR⁷ or N(R³)₂ or —NHCN and W is S or O or N(R⁶) and A is N or CH can be prepared as per below reactions.

Compounds of formula (IIu-3), (IIu-4), (IIu-5) and (IIu-6) can be prepared by heating compounds of formula (IIu-1) with compounds of the formula NH(R³)₂ or NH₂CN or R⁸—OH or R⁷—SH in a polar protic or aprotic solvents in an acidic, basic or neutral conditions as described in WO2010129053, WO2007146824 or Chem. Commun., 2014, 50, 1465.

Compounds of formula (IIv-1), (IIv-2), (IIv-3), (IIv-4), (IIv-5), (IIv-6), (IIv-7), (IIv-8), (IIv-9), (IIv-10), (IIv-11), (IIv-12), (IIv-14), (IIv-15) and (IIv-16), where Q is —C(R⁴R⁵)—O— or —C(R⁷R⁸)—S(═O)_(m) or —O—C(═O)— or —C(R¹⁹R²⁰)—C(═O)— or —N(R²)—S(═O)_(m)— or —N(R²)—C(R⁹R¹⁰)— or —C(═O)—C(R¹⁹R²⁰)— or —N(R²)—C(═O)— or —N(R²)—C(═S)— or —C(R¹³R¹⁴)—C(R¹⁵R¹⁶)— or —N═C(X)— or —N(R²)—C(═NR)— or —O—C(R⁴R⁵)— or —S(═O)_(m)—C(R⁷R⁸)— or —C(═O)—O— and W is S or O or N(R⁶) and A is N and X is OR⁸ or SR⁷ or N(R³)₂ or —NHCN can be prepared from suitable commercially available products following the methods mentioned in the previous schemes.

Individual compounds of formula I can also be prepared by derivatisation of other compounds of formula I or the intermediates thereof.

If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (for example under the action of light, acids or bases). Such conversions may also take place after use, for example in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.

A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the tables below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.

Unless otherwise indicated, the term “compound(s) according to the invention” or “compound(s) of the invention” or “compound(s) of formula (I)”, refers to the compounds of formula I.

The term “compound(s) according to the invention”, or “compounds of formula I” comprises the compound(s) as defined herein as well as a stereoisomer, salt, tautomer or N-oxide thereof. The term “compound(s) of the present invention” is to be understood as equivalent to the term “compound(s) according to the invention”, therefore also comprising a stereoisomer, salt, tautomer or N-oxide thereof.

The term “composition(s) according to the invention” or “composition(s) of the present invention” encompasses composition(s) comprising at least one compound of formula I according to the invention as defined above. The compositions of the invention are preferably agricultural or veterinary compositions.

Depending on the substitution pattern, the compounds according to the invention may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the single pure enantiomers or pure diastereomers of the compounds according to the invention, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds according to the invention or their mixtures. Suitable compounds according to the invention also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond or amide group. The term “stereoisomer(s)” encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers). The present invention relates to every possible stereoisomer of the compounds of formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.

The compounds according to the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention relates to amorphous and crystalline compounds according to the invention, mixtures of different crystalline states of the respective compounds according to the invention, as well as amorphous or crystalline salts thereof.

The term “tautomers” encompasses isomers, which are derived from the compounds of formula I by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, ureaisourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.

The term “stereoisomers” encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).

Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. One center of chirality is the carbon ring atom of the isothiazoline ring carrying radical R¹. The invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures. Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.

The term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO). To be more precise, it relates to any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides of compounds I can in particular be prepared by oxidizing e.g. the ring nitrogen atom of an N-heterocycle, e.g. a pyridine or pyrimidine ring present in Ar or R¹¹, or an imino-nitrogen present in central tricyclic core, with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides. The person skilled in the art knows if and in which positions compounds of the present invention may form N-oxides.

Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.

Suitable agriculturally or veterinarily acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, which are known and accepted in the art for the formation of salts for agricultural or veterinary use respectively, and do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH⁴⁺) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or CH₂-phenyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium. Suitable acid addition veterinarily acceptable salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The term “invertebrate pest” as used herein encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.

The term “plant propagation material” is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. The plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting. Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.

The term “plants” comprises any types of plants including “modified plants” and in particular “cultivated plants”.

The term “modified plants” refers to any wild type species or related species or related genera of a cultivated plant.

The term “cultivated plants” is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://www.bio.org/speeches/pubs/er/agri_products.asp). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e.g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.

Plants that have been modified by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e.g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e.g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e.g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e.g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e.g. WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e.g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus (corn cultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivars producing the Cry1Ac toxin), Bollgard® II (cotton cultivars producing Cry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e.g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the Cry1Ab toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, e.g. EP-A 392 225), plant disease resistance genes (e.g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.g. in the publications mentioned above.

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e.g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera® rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

The organic moieties mentioned in the above definitions of the variables are—like the term halogen—collective terms for individual listings of the individual members. The prefix C_(n)-C_(m) indicates in each case the possible number of carbon atoms in the group.

The term halogen denotes in each case F, Br, Cl or I, in particular F, Cl or Br.

The term “alkyl” as used herein and in the alkyl moieties of alkoxy, alkylthio, and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 (“C₁-C₂-alkyl”), 1 to 3 (“C₁-C₃-alkyl”), 1 to 4 (“C₁-C₄-alkyl”) or 1 to 6 (“C₁-C₆-alkyl”) carbon atoms. C₁-C₂-Alkyl is CH₃ or C₂H₅. C₁-C₃-Alkyl is additionally propyl and isopropyl. C₁-C₄-Alkyl is additionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1,1-dimethylethyl (tert-butyl). C₁-C₆-Alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

The term “haloalkyl” as used herein, which is also expressed as “alkyl which is partially or fully halogenated”, refers to straight-chain or branched alkyl groups having 1 to 2 (“C₁-C₂-haloalkyl”), 1 to 3 (“C₁-C₃-haloalkyl”), 1 to 4 (“C₁-C₄-haloalkyl”) or 1 to 6 (“C₁-C₆-haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular C₁-C₂-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl. C₁-C₃-haloalkyl is additionally, for example, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and the like. Examples for C₁-C₄-haloalkyl are, apart those mentioned for C₁-C₃-haloalkyl, 4-chlorobutyl and the like.

The term “alkylene” (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety. Alkylene has preferably 1 to 6 carbon atoms (C₁-C₆-alkylene), 2 to 6 carbon atoms (C₂-C₆-alkylene), in particular 1 to 4 carbon atoms (C₁-C₄-alkylene) or 2 to 4 carbon atoms (C₂-C₄-alkylene). Examples of alkylene are methylene (CH₂), 1,1-ethandiyl, 1,2-ethandiyl, 1,3-propandiyl, 1,2-propandiyl, 2,2-propandiyl, 1,4-butandiyl, 1,2-butandiyl, 1,3-butandiyl, 2,3-butandiyl, 2,2-butandiyl, 1,5-pentandiyl, 2,2-dimethylpropan-1,3-diyl, 1,3-dimethyl-1,3-propandiyl, 1,6-hexandiyl etc.

The term “alkenyl” as used herein refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C₂-C₃-alkenyl”), 2 to 4 (“C₂-C₄-alkenyl”) or 2 to 6 (“C₂-C₆-alkenyl”) carbon atoms and a double bond in any position, for example C₂-C₃-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl or 1-methylethenyl; C₂-C₄-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl , 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like.

The term “alkynyl” as used herein refers to straight-chain or branched hydrocarbon groups having 2 to 3 (“C₂-C₃-alkynyl”), 2 to 4 (“C₂-C₄-alkynyl”) or 2 to 6 (“C₂-C₆-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C₂-C₃-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; C₂-C₄-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and the like;

The term “cycloalkyl” as used herein refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having in particular 3 to 6 (“C₃-C₆-cycloalkyl”) or 3 to 5 (“C₃-C₅-cycloalkyl”) or 3 to 4 (“C₃-C₄-cycloalkyl”) carbon atoms. Examples of monocyclic radicals having 3 to 4 carbon atoms comprise cyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl. Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.

The term “cycloalkoxy” as used herein refers to a cycloalkyl radical, in particular a monocyclic cycloalkyl radical, as defined above having in particular 3 to 6 (“C₃-C₆-cycloalkoxy”) or 3 to 5 (“C₃-C₅-cycloalkoxy”) or 3 to 4 (“C₃-C₄-cycloalksoxy”) carbon atoms, which is bound via an oxygen atom to the remainder of the molecule.

The term “cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₈-cycloalkyl (“C₃-C₈-cycloalkyl-C₁-C₄-alkyl”), preferably a C₃-C₆-cycloalkyl (“C₃-C₆-cycloalkyl-C₁-C₄-alkyl”), more preferably a C₃-C₄-cycloalkyl (“C₃-C₄-cycloalkyl-C₁-C₄-alkyl”) as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a C₁-C₄-alkyl group, as defined above. Examples for C₃-C₄-cycloalkyl-C₁-C₄-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl, Examples for C₃-C₆-cyclo-alkyl-C₁-C₄-alkyl, apart those mentioned for C₃-C₄-cycloalkyl-C₁-C₄-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.

The term “C₁-C₂-alkoxy” is a C₁-C₂-alkyl group, as defined above, attached via an oxygen atom. The term “C₁-C₃-alkoxy” is a C₁-C₃-alkyl group, as defined above, attached via an oxygen atom. The term “C₁-C₄-alkoxy” is a C₁-C₄-alkyl group, as defined above, attached via an oxygen atom. The term “C₁-C₆-alkoxy” is a C₁-C₆-alkyl group, as defined above, attached via an oxygen atom. The term “C₁-C₁₀-alkoxy” is a C₁-C₁₀-alkyl group, as defined above, attached via an oxygen atom. C₁-C₂-Alkoxy is OCH₃ or OC₂H₅. C₁-C₃-Alkoxy is additionally, for example, n-propoxy and 1-methylethoxy (isopropoxy). C₁-C₄-Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C₁-C₆-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methyl-butoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C₁-C₈-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. C₁-C₁₀-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.

The term “C₁-C₂-haloalkoxy” is a C₁-C₂-haloalkyl group, as defined above, attached via an oxygen atom. The term “C₁-C₃-haloalkoxy” is a C₁-C₃-haloalkyl group, as defined above, attached via an oxygen atom. The term “C₁-C₄-haloalkoxy” is a C₁-C₄-haloalkyl group, as defined above, attached via an oxygen atom. The term “C₁-C₆-haloalkoxy” is a C₁-C₆-haloalkyl group, as defined above, attached via an oxygen atom. C₁-C₂-Haloalkoxy is, for example, OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC₂F₅. C₁-C₃-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-d ifluoropropoxy, 2,3-d ifluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-d ichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy or 1-(CH₂Br)-2-bromoethoxy. C₁-C₄-Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C₁-C₆-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term “C₁-C₆-alkoxy-C₁-C₄-alkyl” as used herein, refers to a straight-chain or branched alkyl having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tertbutoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxy-ethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl, 1-isobutoxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3-tert-butoxypropyl and the like.

The term “alkoxyalkoxy” as used herein refers to an alkoxyalkyl radical, in particular a C₁-C₆-alkoxy-C₁-C₄-alkyl radical, as defined above, which is bound via an oxygen atom to the remainder of the molecule. Examples thereof are OCH₂—OCH₃, OCH₂—OC₂H₅, n-propoxymethoxy, OCH₂—OCH(CH₃)₂, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH₂—OC(CH₃)₃, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, etc.

The substituent “oxo” replaces a CH₂ by a C(═O) group.

The term “aryl” relates to phenyl and bi- or polycyclic carbocycles having at least one fused phenylene ring, which is bound to the remainder of the molecule. Examples of bi- or polycyclic carbocycles having at least one phenylene ring include naphthyl, tetrahydronaphthyl, indanyl, indenyl, anthracenyl, fluorenyl etc.

The term “aryl-C₁-C₄-alkyl” relates to C₁-C₄-alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryl radical, in particular a phenyl radical. Particular examples of aryl-C₁-C₄-alkyl include —CH₂-phenyl, 1-phenethyl, 2-phenetyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl-1-propyl and 2-phenyl-2-propyl.

The term “aryloxy-C₁-C₄-alkyl” relates to C₁-C₄-alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryloxy radical, in particular a phenoxy radical. Particular examples of aryloxy-C₁-C₄-alkyl include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyetyl, 1-phenoxypropyl, 2-phenoxypropyl, 3-phenoxy-1-propyl and 2-phenoxy-2-propyl.

The term “aryl-C₁-C₄-carbonyl” relates to aryl as defined above, in particular a phenyl radical, which is bound by a carbonyl to the remainder of the molecule. Particular examples of arylcarbonyl include benzoyl, 1-naphthoyl and 2-naphthoyl.

The term “hetaryl” relates to aromatic heterocycles having either 5 or 6 ring atoms (5- or 6-membered hetaryl) and being monocyclic or 8, 9 or 10 ring atoms and bing bicyclic. Hetaryl will generally have at least one ring atom selected from O, S and N, which in case of N may be an imino-nitrogen or an amino-nitrogen, which carries hydrogen or a radical different from hydrogen. Hetaryl may have 1, 2, 3 or 4 further nitrogen atoms as ring members, which are imino nitrogens. Examples of 5- or 6-membered hetaryl include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-ox-azolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-oxadiazolyl-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl and 1,3,5-triazin-2-yl. Examples of 8-, 9- or 10-membered hetaryl include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizynyl, isoindolyl, indazolyl, benzofuryl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzimidazolyl, imidazo[1,2-a]pyridine-2-yl, thieno[3,2-b]pyridine-5-yl, imidazo-[2,1-b]-thiazol-6-yl and 1,2,4-triazolo[1,5-a]pyridine-2-yl.

Examples of N-bound 5-, 6-, 7 or 8-membered saturated heterocycles include: pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-4-yl, azepan-1-yl and the like.

The term “hetaryl-C₁-C₄-alkyl” relates to C₁-C₄-alkyl, as defined above, wherein one hydrogen atom has been replaced by a hetaryl radical, in particular a pyridyl radical. Particular examples of hetaryl-C₁-C₄-alkyl include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1-(2-pyridyl)ethyl, 2-(2-pyridyl)ethyl, 1-(3-pyridyl)ethyl, 2-(3-pyridyl)ethyl, 1-(4-pyridyl)ethyl, 2-(4-pyridyl)ethyl etc..

The term “hetaryloxy-C₁-C₄-alkyl” relates to C₁-C₄-alkyl, as defined above, wherein one hydrogen atom has been replaced by an hetaryloxy radical, in particular a pyridyloxy radical. Particular examples of hetaryloxy-C₁-C₄-alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl, 4-pyridyloxymethyl, 1-(2-pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl, 1-(3-pyridyloxy)ethyl, 2-(3-pyridyloxy)ethyl, 1-(4-pyridyloxy)ethyl, 2-(4-pyridyloxy)ethyl etc.

The term “hetaryl-C₁-C₄-carbonyl” relates to hetaryl as defined above, in particular a C-bound hetaryl radical, e.g. 2-, 3-or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl radical, which is bound by a carbonyl to the remainder of the molecule.

The term “substituted” if not specified otherwise refers to substituted with 1, 2 or maximum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not mentioned otherwise.

With respect to the variables, the embodiments of the compounds of the formula I are,

In one preferred embodiment, W is O.

In another preferred embodiment, W is NR⁶.

In another preferred embodiment, W is S(═O)_(m).

In another preferred embodiment, A is CR^(A).

In another preferred embodiment, A is N.

In another preferred embodiment, W is O, A is CR^(A);

In another preferred embodiment, W is O, A is N;

In another preferred embodiment, W is S(═O)_(m), A is CR^(A);

In another preferred embodiment, W is S(═O)_(m), A is N;

In another preferred embodiment, W is NR⁶, A is CR^(A);

In another preferred embodiment, W is NR⁶, A is N;

In one preferred embodiment, B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4);

In another preferred embodiment, B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, B¹ is CR^(B1), B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, B¹ is N, B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, B¹ is N, B² is N, B³ is N, B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is CR^(A), B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is CR^(A), B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is CR^(A), B¹ is CR^(B1), B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is CR^(A), B¹ is N, B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is CR^(A), B¹ is N, B² is N, B³ is N, B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is N, B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is N, B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is N, B¹ is CR^(B1), B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is N, B¹ is N, B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is O, A is N, B¹ is N, B² is N, B³ is N, B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is CR^(A), B1 is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is CR^(A), B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is CR^(A), B¹ is CR^(B1), B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is CR^(A), B¹ is N, B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is CR^(A), B¹ is N, B² is N, B³ is N, B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is N, B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is N, B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is N, B¹ is CR^(B1), B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is N, B¹ is N, B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is S(═O)_(m), A is N, B¹ is N, B² is N, B³ is N, B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is CR^(A), B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is CR^(A), B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is CR^(A), B¹ is CR^(B1), B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is CR^(A), B¹ is N, B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is CR^(A), B¹ is N, B² is N, B³ is N, B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is N, B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is N, B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is N, B¹ is CR^(B1), B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is N, B¹ is N, B² is N, B³ is CR^(B3), B⁴ is CR^(B4);

In another preferred embodiment, W is NR⁶, A is N, B¹ is N, B² is N, B³ is N, B⁴ is CR^(B4);

In one preferred embodiment, R^(A) is H, halogen, OH, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy, tri-C₁-C₆-alkylsilyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, wherein the alkyl, alkoxy, cycloalkyl moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e);

In another preferred embodiment, R^(A) is H, halogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, wherein the alkyl or cycloalkyl moieties are unsubstituted or substituted with halogen.

In another preferred embodiment, R^(A) is H, Cl, Br, F, CH₃, C₂H₅, n-C₃H₇, isopropyl, cyclopropyl, CH₂F, CHF₂, or CF₃.

In one preferred embodiment, R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are H, halogen, or C₁-C₆-alkyl;

In another preferred embodiment, R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are H, Cl, Br, F, CH₃, C₂H₅, n-C₃H₇, or isopropyl.

In one preferred embodiment, Q is —C(R⁴R⁵)—O—, wherein C is bound to Ar.

In another preferred embodiment, Q is —C(R⁴R⁵)—O—, wherein O is bound to Ar.

In another preferred embodiment, Q is —C(═O)—O—, wherein C is bound to Ar.

In another preferred embodiment, Q is —C(═O)—O—, wherein O is bound to Ar.

In another preferred embodiment, Q is —S(═O)_(m)—C(R⁷R⁸)—, wherein S is bound to Ar.

In another preferred embodiment, Q is —S(═O)_(m)—C(R⁷R⁸)—, wherein C is bound to Ar.

In another preferred embodiment, Q is —N(R²)—S(═O)_(m)—, wherein N is bound to Ar.

In another preferred embodiment, Q is —N(R²)—S(═O)_(m)—, wherein S is bound to Ar.

In another preferred embodiment, Q is —N(R²)—C(R⁹R¹⁰)—, wherein N is bound to Ar.

In another preferred embodiment, Q is —N(R²)—C(R⁹R¹⁰)—, wherein C is bound to Ar.

In another preferred embodiment, Q is —C(═O)—C(R¹⁹R²⁰)—, wherein C(═O) is bound to Ar.

In another preferred embodiment, Q is —C(═O)—C(R¹⁹R²⁰)—, wherein C(R¹⁹R²⁰) is bound to Ar.

In another preferred embodiment, Q is —N(R²)—C(═O)—, wherein N is bound to Ar.

In another preferred embodiment, Q is —N(R²)—C(═O)—, wherein C is bound to Ar.

In another preferred embodiment, Q is —N(R²)—C(═S)—, wherein N is bound to Ar.

In another preferred embodiment, Q is —N(R²)—C(═S)—, wherein C is bound to Ar.

In another preferred embodiment, Q is —N═C(X)—, wherein N is bound to Ar.

In another preferred embodiment, Q is —N═C(X)—, wherein C is bound to Ar.

In another preferred embodiment, Q is —N(R²)—C(═NR)—, wherein N is bound to Ar.

In another preferred embodiment, Q is —N(R²)—C(═NR)—, wherein C is bound to Ar.

In another preferred embodiment, Q is —C(R¹³R¹⁴)—C(R¹⁵R¹⁶)—.

In another preferred embodiment, Q is —C(R⁴R⁵)—O—, —N(R²)—S(═O)_(m)—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═S)—, —N═C(X)—, or —N(R²)—C(═NR)—, wherein Ar is bound to either side of Q;

In another preferred embodiment, Q is —C(R⁴R⁵)—O—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═NR)—, wherein Ar is bound to either side of Q;

In one preferred embodiment, X is H or N(R³)₂;

In another preferred embodiment, X is H;

In another preferred embodiment, X is N(R³)₂, preferably NH₂ or N(CH₃)₂;

In one preferred embodiment, R³ is H, C₁-C₆-alkyl, or C₁-C₆-alkoxy-C₁-C₄-alkyl;

In another preferred embodiment, R³ is H, or C₁-C₆-alkyl;

In another preferred embodiment, R³ is C₁-C₆-alkyl;

In another preferred embodiment, R³ is H;

In one preferred embodiment, R is H, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, OR⁸, or N(R³)₂;

In another preferred embodiment, R is H, CN, C₁-C₆-alkyl, or OR⁸;

In another preferred embodiment, R is H, or C₁-C₆-alkyl;

In another preferred embodiment, R is H, CH₃, C₂H₅, n-C₃H₇, or isopropyl;

In one preferred embodiment, R⁶ is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f);

In another preferred embodiment, R⁶ is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

In another preferred embodiment, R⁶ is C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f);

In another preferred embodiment, R⁶ is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, —CH₂—C(═O)—OR^(a), or —CH₂-phenyl;

In another preferred embodiment, R⁶ is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, or —CH₂-phenyl;

In another preferred embodiment, R⁶ is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, or —CH₂—C(═O)—OR^(a);

In another preferred embodiment, R⁶ is H, C₁-C₆-alkyl, or C₁-C₆-haloalkyl;

In another preferred embodiment, R⁶ is H;

In another preferred embodiment, R⁶ is C₁-C₆-alkyl;

In another preferred embodiment, R⁶ is C₁-C₆-haloalkyl;

In another preferred embodiment, R⁶ is H, CH₃, C₂H₅, CH₂CF₃, or CHF₂;

In another preferred embodiment, R⁶ is H, CH₃, C₂H₅, or CH₂CF₃;

In one preferred embodiment, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁹, R²⁰ are, identical or different, H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkylalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, C(═O)—OR^(a), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f);

In another preferred embodiment, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁹, R²⁰ are, identical or different, H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkylalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halo-cycloalkyl, C(═O)—OR^(a), C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f);

In another preferred embodiment, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁹, R²⁰ are, identical or different, H, halogen, C₁-C₆-alkyl, or C₁-C₆-haloalkylalkyl;

In another preferred embodiment, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁹, R²⁰ are, identical or different, H, halogen, or C₁-C₆-alkyl;

In another preferred embodiment, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁹, R²⁰ are, identical or different, H or C₁-C₆-alkyl;

In one preferred embodiment, Ar is phenyl which is unsubstituted or substituted with R^(Ar).

In another preferred embodiment, Ar is 5- or 6-membered hetaryl, which is unsubstituted or substituted with R^(Ar).

In more preferred embodiment, Ar is phenyl, pyrimidinyl, pyridazinyl, or pyridyl, which are unsubstituted or substituted with R^(Ar).

In one preferred embodiment, R^(Ar) is halogen, OH, CN, NO₂, SCN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, or S—R^(e).

In more preferred embodiment, R^(Ar) is F, Cl, Br, OH, CN, NO₂, SCN, CH₃, C₂H₅, n-C₃H₇, isopropyl, CH₂F, CHF₂, CF₃, CH₂CF₃, CF₂CHF₂, C₂F₅, CH₂CH₂CF₃, CH₂CF₂CHF₂, CH₂CF₂CF₃, OCH₃, OC₂H₅, n-propyloxy, isopropyloxy, OCH₂F, OCHF₂, OCF₃, OCH₂CF₃, OCF₂CHF₂, OC₂F₅, OCH₂CH₂CF₃, OCH₂CF₂CHF₂, OCH₂CF₂CF₃, or S—R^(e), where R^(e) is C₁-C₆-alkyl, in particular C₁-C₃-alkyl such as CH₃, C₂H₅, n-C₃H₇ or isopropyl, or C₁-C₆-haloalkyl, in particular fluorinated C₁-C₃-alkyl such as CH₂F, CHF₂, CF₃, CH₂CF₃, CF₂CHF₂, C₂F₅, CH₂CH₂CF₃, CH₂CF₂CHF₂ or CH₂CF₂CF₃.

Particularly preferred Ar are listed in Table A below.

TABLE A

Ar-1

Ar-2

Ar-3

Ar-4

Ar-5

Ar-6

Ar-7

Ar-8

Ar-9

Ar-10

Ar-11

Ar-12

Ar-13

Ar-14

Ar-15

Ar-16

Ar-17

Ar-18

Ar-19

Ar-20

Ar-21

Ar-22

Particularly preferred Ar is selected from Ar-1 to Ar-20;

also particularly preferred Ar is selected from Ar-1 to Ar-13;

also particularly preferred Ar is selected from Ar-1 to Ar-13 and Ar-17 to Ar-18;

also particularly preferred Ar is selected from Ar-1, Ar-2, Ar-3, Ar-4, Ar-10, Ar-17, and Ar-18.

also particularly preferred Ar is selected from Ar-17 and Ar-18;

also particularly preferred Ar is Ar-17;

also particularly preferred Ar is Ar-18;

In one preferred embodiment, R¹ is Y—Z-T-R¹¹.

In another preferred embodiment, R¹ is Y—Z-T-R¹².

In one preferred embodiment, Y is —CR^(ya)═N—, wherein the N is bound to Z.

In another preferred embodiment, Y is —NR^(yc)—C(═S)—, wherein C(═S) is bound to Z.

In another preferred embodiment, Y is —NR^(yc)—C(═O)—, wherein C(═O) is bound to Z.

In one preferred embodiment, Z is a single bond;

—NR^(zc)—C(═O)—, wherein C(═O) is bound to T;

—NR^(zc)—C(═S)—, wherein C(═S) is bound to T;

—N═C(S—R^(za))—, wherein T is bound to the carbon atom; or

—N R^(zc)—C(S—R^(za))═, wherein T is bound to the carbon atom;

In another preferred embodiment, Z is —NR^(zc)—C(═S)—, wherein C(═S) is bound to T.

In another preferred embodiment, Z is —NR^(zc)—C(═O)—, wherein C(═O) is bound to T.

In another preferred embodiment, Z is —N═C(S—R^(za))—, wherein T is bound to the carbon atom.

In another preferred embodiment, Z is —NR^(zc)—C(S—R^(za))═, wherein T is bound to the carbon atom.

In another preferred embodiment, Z is —O—C(═O)—, wherein T is bound to the carbon atom;

In another preferred embodiment, Z is a single bond.

In one preferred embodiment, T is O.

In another preferred embodiment, T is N—R^(T).

In another preferred embodiment, T is N.

In one preferred embodiment, R^(ya) is H, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, which are unsubstituted or substituted with halogen, phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f).

In more preferred embodiment, R^(ya) is H, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, which are unsubstituted or substituted with halogen, or phenyl which is unsubstituted or substituted with R^(f).

In most preferred embodiment, R^(ya) is H, F, Cl, Br, CH₃, C₂H₅, n-C₃H₇, isopropyl, CH₂F, CHF₂, CF₃, CH₂CF₃, CF₂CHF₂, C₂F₅, CH₂CH₂CF₃, CH₂CF₂CHF₂, CH₂CF₂CF₃, OCH₃, OC₂H₅, n-propyloxy, isopropyloxy, OCH₂F, OCHF₂, OCF₃, OCH₂CF₃, OCF₂CHF₂, OC₂F₅, OCH₂CH₂CF₃, OCH₂CF₂CHF₂, OCH₂CF₂CF₃, or phenyl which is unsubstituted or substituted with R^(f).

In further most preferred embodiment, R^(ya) is H or CH₃;

In one embodiment, R^(yc), R^(zc) are H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, which are unsubstituted or substituted with halogen, phenyl, or —CH₂-phenyl, wherein the rings are unsubstituted or substituted with R^(f).

In more preferred embodiment, R^(yc) and R^(zc) are H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, or phenyl which is unsubstituted or substituted with R^(f).

In most preferred embodiment, R^(yc) and R^(zc) are H, CH₃, C₂H₅, n-C₃H₇, isopropyl, CH₂F, CHF₂, CF₃, CH₂CF₃, CF₂CHF₂, C₂F₅, CH₂CH₂CF₃, CH₂CF₂CHF₂, CH₂CF₂CF₃, or phenyl which is unsubstituted or substituted with R^(f).

In further most preferred embodiment, R^(yc) and R^(zc) are H or CH₃;

In one preferred embodiment, R^(T) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy, which are unsubstituted or substituted with halogen, C(═O)—NR^(b)R^(c), C(═O)R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f).

In more preferred embodiment, R^(T) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy, which are unsubstituted or substituted with halogen.

In most preferred embodiment, R^(T) is H or C₁-C₆-alkyl.

In another preferred embodiment, R^(zc) together with R^(T) if present, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂ moieties may be replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h).

In more preferred embodiment, R^(zc) together with R^(T) if present, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety is replaced by a carbonyl group.

In another more preferred embodiment, R^(zc) together with R^(T) if present, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety is replaced by a C═N—R′ and wherein 1 or 2 CH₂ moieties may be replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h).

In another more preferred embodiment, R^(zc) together with R^(T) if present, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene 1 or 2 CH₂ moieties are replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h).

In one preferred embodiment, R^(za) is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-C(═O)—R^(d), phenyl, phenylcarbonyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f);

In more preferred embodiment, R^(za) is H, C₁-C₆-alkyl, or C₁-C₆-haloalkyl;

In most preferred embodiment, R^(za) is H, C₁-C₆-alkyl.

In another preferred embodiment, R^(za) together with R^(T) if present, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂ moieties may be replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h);

In more preferred embodiment, R^(za) together with R^(T) if present, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety is replaced by a carbonyl group.

In another more preferred embodiment, R^(za) together with R^(T) if present, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety is replaced by a C═N—R′ and wherein 1 or 2 CH₂ moieties may be replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h).

In another more preferred embodiment, R^(za) together with R^(T) if present, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene 1 or 2 CH₂ moieties are replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h).

In a preferred embodiment, R^(a), R^(b) and R^(c) are H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, which are unsubstituted or substituted with halogen, C₁-C₆-alkylene-CN, phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f);

In more preferred embodiment, R^(a), R^(b) and R^(c) are H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, which are unsubstituted or substituted with halogen, phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f).

In a preferred embodiment, R^(e) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, which are unsubstituted or substituted with halogen, phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f).

In more preferred embodiment, R^(e) is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, or phenyl which is unsubstituted or substituted with R^(f).

In one preferred embodiment, R^(e) is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f).

In more preferred embodiment, R^(e) is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, or phenyl unsubstituted or substituted with R^(f).

In one preferred embodiment, R^(f) is halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, which are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e).

In more preferred embodiment, R^(f) is halogen, N₃, OH, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, which are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e).

In a preferred embodiment, R^(g) is halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, which are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e).

In more preferred embodiment, R^(g) is halogen, N₃, OH, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, which are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e).

In one embodiment, m is 0.

In another embodiment, m is 1.

In another embodiment, m is 2.

In another embodiment, m is 0 or 1.

In another embodiment, m is 1 or 2.

In more preferred embodiment, R¹ are formulas Y-1 to Y-9 wherein

denotes attachment to the 6 membered ring, D is R¹¹ or R¹² and wherein R^(T), R¹¹, R¹², R^(ya), R^(yc), R^(za) and R^(zc) are as defined in compounds of formula I.

In more preferred embodiment, R¹ are formulas Y-1 to Y-8 wherein

denotes attachment to the 6 membered ring, D is R¹¹ or R¹² and wherein R^(T), R¹¹, R¹², R^(ya), R^(yc), R^(za) and R^(zc) are as defined in compounds of formula I.

In another more preferred embodiment, R¹ are formulas YZT-1 to YZT-9, wherein

denotes attachment to the 6 membered ring and R¹¹, R¹², R^(T), R^(ya), R^(za) and R^(zc) are as defined in compounds of formula I.

In another more preferred embodiment, R¹ are formulas YZT-1 to YZT-8, wherein

denotes attachment to the 6 membered ring and R¹¹, R¹², R^(T), R^(ya), R^(za) and R^(zc) are as defined in compounds of formula I.

In most preferred embodiment, R¹ are formulas Y-1A to Y-9A, wherein

denotes attachment to the 6 membered ring, D is R¹¹ or R¹².

In most preferred embodiment, R¹ are formulas Y-1A to Y-8B, wherein

denotes attachment to the 6 membered ring, D is R¹¹ or R¹².

In one preferred embodiment, R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, which are unsubstituted or substituted with halogen, aryl, arylcarbonyl, aryloxy-C₁-C₄-alkyl, hetaryl, carbonylhetaryl, C₁-C₄-alkyl-hetaryl and C₁-C₄-alkyl-hetaryloxy, wherein the aryl or hetaryl rings are unsubstituted or substituted with R^(g) and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl.

In more preferred embodiment, R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, which are unsubstituted or substituted with halogen, aryl, arylcarbonyl, aryloxy-C₁-C₄-alkyl, hetaryl, carbonylhetaryl, C₁-C₄-alkyl-hetaryl and C₁-C₄-alkyl-hetaryloxy, where the rings are unsubstituted or substituted with R^(g) and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl.

In most preferred embodiment, R¹¹ is aryl, aryl-C₁-C₄-alkyl, hetaryl, or hetaryl-C₁-C₄-alkyl, wherein the rings are unsubstituted or substituted with R^(g) and where hetaryl in hetaryl or hetaryl-C₁-C₄-alkyl, is preferably a 5- or 6-membered monocyclic hetaryl such as pyridyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl which is unsubstituted or substituted with R^(g).

Examples of particularly preferred radicals R¹¹ are the radicals R¹¹-1 to R¹¹-29 summarized in Table A-1 below.

TABLE A-1

R¹¹-1

R¹¹-2

R¹¹-3

R¹¹-4

R¹¹-5

R¹¹-6

R¹¹-7

R¹¹-8

R¹¹-9

R¹¹-10

R¹¹-11

R¹¹-12

R¹¹-13

R¹¹-14

R¹¹-15

R¹¹-16

R¹¹-17

R¹¹-18

R¹¹-19

R¹¹-20

R¹¹-21

R¹¹-22

R¹¹-23

R¹¹-24

R¹¹-25

R¹¹-26

R¹¹-27

R¹¹-28

R¹¹-29

In one embodiment, R¹² is a radical of the formula (A¹),

wherein # indicates the point of attachment to T and wherein R¹²¹, R¹²², R¹²³ and R¹²⁴ are as defined above and wherein R¹²¹, R¹²², R¹²³ and R¹²⁴ independently of each other and especially in combination preferably have the following meanings:

-   -   R¹²¹ is C₁-C₄-alkoxy, in particular OCH₃, OC₂H₅;     -   R¹²² is C₁-C₄-alkoxy, such as OCH₃, OC₂H₅, n-propoxyx or         isopropoxy, or C₃-C₄-alkenyloxy, such as allyloxy, with R¹²² in         particular being OCH₃, OC₂H₅, or n-propoxy;     -   R¹²³ is OH, C₁-C₄-alkoxy, such as OCH₃, OC₂H₅, or         C₃-C₄-alkenyloxy, such as allyloxy, with R¹²³ in particular         being OCH₃, OC₂H₅;     -   R¹²⁴ is C₁-C₄-alkyl, such as CH₃ or C₂H₅, or         C₁-C₄-alkoxy-C₁-C₄-alkyl, such as methoxymethyl, ethoxymethyl,         2-methoxyethyl or 2-ethoxyethyl, with R¹²⁴ in particular being         methyl;.

In more preferred embodiment, R¹² is in particular a radical of the formula (A¹¹), e.g. (A¹¹-a) or (A¹¹-b)

wherein # indicates the point of attachment to T and wherein R¹²¹, R¹²², R¹²³ and R¹²⁴ are as defined above and wherein R¹²¹, R¹²², R¹²³ and R¹²⁴ independently of each other and especially in combination preferably have the following meanings:

-   -   R¹²¹ is C₁-C₄-alkoxy, in particular OCH₃ or OC₂H₅;     -   R¹²² is C₁-C₄-alkoxy, such as OCH₃, OC₂H₅, n-propoxyx or         isopropoxy, or C₃-C₄-alkenyloxy, such as allyloxy, with R¹²² in         particular being OCH₃, OC₂H₅ or n-propoxy;     -   R¹²³ is OH, C₁-C₄-alkoxy, such as OCH₃ or OC₂H₅, or         C₃-C₄-alkenyloxy, such as allyloxy, with R¹²³ in particular         being OCH₃ or OC₂H₅;     -   R¹²⁴ is C₁-C₄-alkyl, such as CH₃ or C₂H₅, or         C₁-C₄-alkoxy-C₁-C₄-alkyl, such as methoxymethyl, ethoxymethyl,         2-methoxyethyl or 2-ethoxyethyl, with R¹²⁴ in particular being         methyl.

Particular examples of radicals R¹² are the following radicals A¹¹-1, A¹¹-1a, A¹¹-1b, A¹¹-2, A¹¹-2a, A¹¹-2b, A¹¹-3, A¹¹-3a and A¹¹-3b:

In a more preferred embodiment compounds of formula I are selected from compounds of formula A.1 to A.50.

wherein, Ar is phenyl or 5- or 6-membered hetaryl ring which is substituted with R^(Ar);

R^(Ar) is halogen, OH, CN, NO₂, SCN, C₁-C₆-alkyl, C₁-C₆-alkoxy, or S—R^(e), wherein the alkyl and alkoxy are unsubstituted or substituted with halogen;

R^(A) is H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, or C₃-C₆-halocycloalkyl;

R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are H, halogen, or C₁-C₆-alkyl;

Q is —C(R⁴R⁵)—O—, —N(R²)—S(═O)_(m)—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═S)—, —N═C(X)—, —N(R²)—C(═NR)—; wherein Ar is bound to either side of Q;

X is N(R³)₂;

and R¹ is Y—Z-T-R¹¹ or Y—Z-T-R¹², as defined in formula I.

more preferred compounds of formula I are compounds of formula I.1 to I.24, wherein R¹ is selected from Y-1A, Y-1B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C, Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8A, and Y-8B; wherein D is R¹¹ or R¹², and other variables are as defined herein.

Also more preferred are the compound of formula I, wherein

A CR^(A);

W is O, S(═O)_(m), or NR⁶;

B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4)

R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are H, halogen, C₁-C₆-alkyl;

Q is —C(R⁴R⁵)—O—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═NR)—; wherein Ar is bound to either side of Q;

m is 0, 1, or 2;

R is H, CN, or C₁-C₆-alkyl;

R² is H or C₁-C₆-alkyl;

R⁴, R⁵, R⁹, R¹⁰, are identical or different H or C₁-C₆-alkyl;

R⁶ is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, or CH₂-phenyl;

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar¹⁰, Ar¹⁷, or Ar¹⁸;

R¹ is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A, or Y-9A;

D is R¹¹ or R¹²;

R¹¹ is R¹¹-1 or R¹¹-10;

R¹² is A¹¹-1b or A¹¹-3b;

Also more preferred are the compound of formula I, wherein

A N;

W is O, S(═O)_(m), or NR⁶;

B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4)

R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are H, halogen, C₁-C₆-alkyl;

Q is —C(R⁴R⁵)—O—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═NR)—; wherein Ar is bound to either side of Q;

m is 0, 1, or 2;

R is H, CN, or C₁-C₆-alkyl;

R² is H or C₁-C₆-alkyl;

R⁴, R⁵, R⁹, R¹⁰, are identical or different H or C₁-C₆-alkyl;

R⁶ is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl, or —CH₂-phenyl;

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar¹⁰, Ar¹⁷, or Ar¹⁸;

R¹ is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A, or Y-9A;

D is R¹¹ or R¹²;

R¹¹ is R¹¹-1 or R¹¹-10;

R¹² is A¹¹-1b or A¹¹-3b;

Also more preferred are the compound of formula I, wherein

A N or R^(A);

W is O, S, NH, N—CH₃, N—CH(CH₃)₂, N—CH₂(C₆H₅), N—CH₂CHF₂, or N—C₂H₅;

B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4)

R^(A) is H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, or C₃-C₆-halocycloalkyl;

R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are H, halogen, C₁-C₆-alkyl;

Q is —C(R⁴R⁵)—O—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═NR)—; wherein Ar is bound to either side of Q;

R is H, CN, or C₁-C₆-alkyl;

R² is H or C₁-C₆-alkyl;

R⁴, R⁵, R⁹, R¹⁰, are identical or different H or C₁-C₆-alkyl;

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar¹⁰, Ar¹⁷, or Ar¹⁸;

R¹ is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A, or Y-9A;

D is R¹¹ or R¹²;

R¹¹ is R¹¹-1 or R¹¹-10;

R¹² is A¹¹-1b or A¹¹-3b;

Also more preferred are the compound of formula I, wherein

A N or R^(A);

W is O, S, NH, N—CH₃, N—CH(CH₃)₂, N—CH₂(C₆H₅), N—CH₂CHF₂, or N—C₂H₅;

B¹ is CR^(B1), B² is N, B³ is CR^(B3), and B⁴ is CR^(B4)

R^(A) is H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, or C₃-C₆-halocycloalkyl;

R^(B1), R^(B3), and R^(B4) independently of each other are H, halogen, C₁-C₆-alkyl;

Q is —C(R⁴R⁵)—O—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═NR)—; wherein Ar is bound to either side of Q;

R is H, CN, or C₁-C₆-alkyl;

R² is H or C₁-C₆-alkyl;

R⁴, R⁵, R⁹, R¹⁰, are identical or different H or C₁-C₆-alkyl;

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar¹⁰, Ar¹⁷, or Ar¹⁸;

R¹ is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A, or Y-9A;

D is R¹¹ or R¹²;

R¹¹ is R¹¹-1 or R¹¹-10;

R¹² is A¹¹-1b or A¹¹-3b;

Also more preferred are the compound of formula I, wherein

A N or R^(A);

W is O, S, NH, N—CH₃, N—CH(CH₃)₂, N—CH₂(C₆H₅), N—CH₂CHF₂, or N—C₂H₅;

B¹ is CR^(B1), B² is N, B³ is N, and B⁴ is CR^(B4)

R^(A) is H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, or C₃-C₆-halocycloalkyl;

R^(B1), R^(B3), and R^(B4) independently of each other are H, halogen, C₁-C₆-alkyl;

Q is —C(R⁴R⁵)—O—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═NR)—; wherein Ar is bound to either side of Q;

R is H, CN, or C₁-C₆-alkyl;

R² is H or C₁-C₆-alkyl;

R⁴, R⁵, R⁹, R¹⁰, are identical or different H or C₁-C₆-alkyl;

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar¹⁰, Ar¹⁷, or Ar¹⁸;

R¹ is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A, or Y-9A;

D is R¹¹ or R¹²;

R¹¹ is R¹¹-1 or R¹¹-10;

R¹² is A¹¹-1b or A¹¹-3b;

Also more preferred are the compound of formula I, wherein

A N or R^(A);

W is O, S, NH, N—CH₃, N—CH(CH₃)₂, N—CH₂(C₆H₅), N—CH₂CHF₂, or N—C₂H₅;

B¹ is N, B² is N, B³ is CR^(B3), and B⁴ is CR^(B4)

R^(A) is H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, or C₃-C₆-halocycloalkyl;

R^(B3), and R^(B4) independently of each other are H, halogen, C₁-C₆-alkyl;

Q is —C(R⁴R⁵)—O—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═NR)—; wherein Ar is bound to either side of Q;

R² is H or C₁-C₆-alkyl;

R is H, CN, or C₁-C₆-alkyl;

R⁴, R⁵, R⁹, R¹⁰, are identical or different H or C₁-C₆-alkyl;

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar¹⁰, Ar¹⁷, or Ar¹⁸;

R¹ is Y-1A, Y-3C, Y-5A, Y-6A, Y-7A, Y-8A, or Y-9A;

D is R¹¹ or R¹²;

R¹¹ is R¹¹-1 or R¹¹-10;

R¹² is A¹¹-1b or A¹¹-3b;

In another preferred embodiment, the compound of formula I are compounds of formula I.1 to I.24, wherein

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar¹⁰, Ar¹⁷, or Ar¹⁸;

B¹ is N or CH;

B² is N or CH;

B³ is N or CH;

W is NH, NCH₃, NC₂H₅, O, or S;

R¹ is Y-1A, Y-1 B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C, Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8A, or Y-8B; wherein D is R¹¹ or R¹²;

R¹¹ is R¹¹-1, R¹¹-2, R¹¹-3, R¹¹-5, R¹¹-6, R¹¹-7, R¹¹-8, R¹¹-9, R¹¹-10, R¹¹-1 1, R¹¹-12, R¹¹-13, R¹¹-14, R¹¹-15, R¹¹-16, R¹¹-17, R¹¹-18, R¹¹-19, R¹¹-20, R¹¹-21, R¹¹-22, R¹¹-23, R¹¹-25, R¹¹- 26, R¹¹-27, R¹¹-28, or R¹¹-29;

R¹² is (A¹¹-1), (A¹¹-2), or (A¹¹-3).

R⁴ and R⁵ independently are H or CH₃,

R⁹ and R¹⁰ independently are H or CH₃,

R² is H, CH₃, or c-C₃H₅

R is NH, NCH₃, or NCN;

In another preferred embodiment, the compound of formula I are compounds wherein Ar is Ar¹, Ar², Ar⁴, Ar¹⁰, Ar¹⁸, Ar²¹, or Ar²²;

Q is —C(R⁴R⁵)—O—, —N(R²)—C(R⁹R¹⁰)—, —N(R²)—C(═O)—, or —N═C(X)—; wherein Ar is bound to either side of Q;

R² is H or C₁-C₆-alkyl;

R⁴, R⁵, R⁹, R¹⁰, are identical or different H or C₁-C₆-alkyl;

B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4)

R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are H, halogen, C₁-C₆-alkyl;

A is CR^(A) or N, wherein R^(A) is selected from CH, CH₃, and Cl;

W is NH, NCH₃, or NC₂H₅;

R¹ is Y-1A, Y-5A, Y-6A, or Y-7A; wherein D is R¹¹ or R¹²;

R¹¹ is R¹¹-1 or R¹¹-29;

R¹² is A¹¹ wherein R¹²¹, R¹²², R¹²³, R¹²⁴ independently are selected from OCH₃, OC₂H₅, and O-nC₃H₇;

R⁴ and R⁵ independently are H or CH₃,

R⁹ and R¹⁰ independently are H or CH₃,

R² is H, CH₃, or c-C₃H₅

X is H, NH₂ or N(CH₃)₂;

Particular compounds of formula I are the compounds of the formulae I.1 to I.24 that are compiled in the following tables 1 to 3240, wherein the combination of variables W, B¹, B², B³, Ar, and D for each compound of tables 1 to 3240 corresponds to each line of Table B. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.

Table 1. Compounds of formula I.1 wherein R¹ is Y-1A, R⁴ is H and R⁵ is H.

Table 2. Compounds of formula I.1 wherein R¹ is Y-1B, R⁴ is H and R⁵ is H.

Table 3. Compounds of formula I.1 wherein R¹ is Y-2A, R⁴ is H and R⁵ is H.

Table 4. Compounds of formula I.1 wherein R¹ is Y-2B, R⁴ is H and R⁵ is H.

Table 5. Compounds of formula I.1 wherein R¹ is Y-3A, R⁴ is H and R⁵ is H.

Table 6. Compounds of formula I.1 wherein R¹ is Y-3B, R⁴ is H and R⁵ is H.

Table 7. Compounds of formula I.1 wherein R¹ is Y-3C, R⁴ is H and R⁵ is H.

Table 8. Compounds of formula I.1 wherein R¹ is Y-3D, R⁴ is H and R⁵ is H.

Table 9. Compounds of formula I.1 wherein R¹ is Y-4A, R⁴ is H and R⁵ is H.

Table 10. Compounds of formula I.1 wherein R¹ is Y-4B, R⁴ is H and R⁵ is H.

Table 11. Compounds of formula I.1 wherein R¹ is Y-4C, R⁴ is H and R⁵ is H.

Table 12. Compounds of formula I.1 wherein R¹ is Y-4D, R⁴ is H and R⁵ is H.

Table 13. Compounds of formula I.1 wherein R¹ is Y-5A, R⁴ is H and R⁵ is H.

Table 14. Compounds of formula I.1 wherein R¹ is Y-5B, R⁴ is H and R⁵ is H.

Table 15. Compounds of formula I.1 wherein R¹ is Y-6A, R⁴ is H and R⁵ is H.

Table 16. Compounds of formula I.1 wherein R¹ is Y-6B, R⁴ is H and R⁵ is H.

Table 17. Compounds of formula I.1 wherein R¹ is Y-7A, R⁴ is H and R⁵ is H.

Table 18. Compounds of formula I.1 wherein R¹ is Y-7B, R⁴ is H and R⁵ is H.

Table 19. Compounds of formula I.1 wherein R¹ is Y-8A, R⁴ is H and R⁵ is H.

Table 20. Compounds of formula I.1 wherein R¹ is Y-8B, R⁴ is H and R⁵ is H.

Table 21. Compounds of formula I.1 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is H.

Table 22. Compounds of formula I.1 wherein R¹ is Y-1B, R⁴ is CH₃ and R⁵ is H.

Table 23. Compounds of formula I.1 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is H.

Table 24. Compounds of formula I.1 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is H.

Table 25. Compounds of formula I.1 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is H.

Table 26. Compounds of formula I.1 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is H.

Table 27. Compounds of formula I.1 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is H.

Table 28. Compounds of formula I.1 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is H.

Table 29. Compounds of formula I.1 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is H.

Table 30. Compounds of formula I.1 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is H.

Table 31. Compounds of formula I.1 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is H.

Table 32. Compounds of formula I.1 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is H.

Table 33. Compounds of formula I.1 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is H.

Table 34. Compounds of formula I.1 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is H.

Table 35. Compounds of formula I.1 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is H.

Table 36. Compounds of formula I.1 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is H.

Table 37. Compounds of formula I.1 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is H.

Table 38. Compounds of formula I.1 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is H.

Table 39. Compounds of formula I.1 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is H.

Table 40. Compounds of formula I.1 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is H.

Table 41. Compounds of formula I.1 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is CH₃.

Table 42. Compounds of formula I.1 wherein R¹ is Y-1B, R⁴ is CH₃ and R⁵ is CH₃.

Table 43. Compounds of formula I.1 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is CH₃.

Table 44. Compounds of formula I.1 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is CH₃.

Table 45. Compounds of formula I.1 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is CH₃.

Table 46. Compounds of formula I.1 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is CH₃.

Table 47. Compounds of formula I.1 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is CH₃.

Table 48. Compounds of formula I.1 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is CH₃.

Table 49. Compounds of formula I.1 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is CH₃.

Table 50. Compounds of formula I.1 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is CH₃.

Table 51. Compounds of formula I.1 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is CH₃.

Table 52. Compounds of formula I.1 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is CH₃.

Table 53. Compounds of formula I.1 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is CH₃.

Table 54. Compounds of formula I.1 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is CH₃.

Table 55. Compounds of formula I.1 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is CH₃.

Table 56. Compounds of formula I.1 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is CH₃.

Table 57. Compounds of formula I.1 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is CH₃.

Table 58. Compounds of formula I.1 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is CH₃.

Table 59. Compounds of formula I.1 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is CH₃.

Table 60. Compounds of formula I.1 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is CH₃.

Table 61. Compounds of formula I.2 wherein R¹ is Y-1A, R⁴ is H and R⁵ is H.

Table 62. Compounds of formula I.2 wherein R¹ is Y-1 B, R⁴ is H and R⁵ is H.

Table 63. Compounds of formula I.2 wherein R¹ is Y-2A, R⁴ is H and R⁵ is H.

Table 64. Compounds of formula I.2 wherein R¹ is Y-2B, R⁴ is H and R⁵ is H.

Table 65. Compounds of formula I.2 wherein R¹ is Y-3A, R⁴ is H and R⁵ is H.

Table 66. Compounds of formula I.2 wherein R¹ is Y-3B, R⁴ is H and R⁵ is H.

Table 67. Compounds of formula I.2 wherein R¹ is Y-3C, R⁴ is H and R⁵ is H.

Table 68. Compounds of formula I.2 wherein R¹ is Y-3D, R⁴ is H and R⁵ is H.

Table 69. Compounds of formula I.2 wherein R¹ is Y-4A, R⁴ is H and R⁵ is H.

Table 70. Compounds of formula I.2 wherein R¹ is Y-4B, R⁴ is H and R⁵ is H.

Table 71. Compounds of formula I.2 wherein R¹ is Y-4C, R⁴ is H and R⁵ is H.

Table 72. Compounds of formula I.2 wherein R¹ is Y-4D, R⁴ is H and R⁵ is H.

Table 73. Compounds of formula I.2 wherein R¹ is Y-5A, R⁴ is H and R⁵ is H.

Table 74. Compounds of formula I.2 wherein R¹ is Y-5B, R⁴ is H and R⁵ is H.

Table 75. Compounds of formula I.2 wherein R¹ is Y-6A, R⁴ is H and R⁵ is H.

Table 76. Compounds of formula I.2 wherein R¹ is Y-6B, R⁴ is H and R⁵ is H.

Table 77. Compounds of formula I.2 wherein R¹ is Y-7A, R⁴ is H and R⁵ is H.

Table 78. Compounds of formula I.2 wherein R¹ is Y-7B, R⁴ is H and R⁵ is H.

Table 79. Compounds of formula I.2 wherein R¹ is Y-8A, R⁴ is H and R⁵ is H.

Table 80. Compounds of formula I.2 wherein R¹ is Y-8B, R⁴ is H and R⁵ is H.

Table 81. Compounds of formula I.2 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is H.

Table 82. Compounds of formula I.2 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is H.

Table 83. Compounds of formula I.2 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is H.

Table 84. Compounds of formula I.2 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is H.

Table 85. Compounds of formula I.2 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is H.

Table 86. Compounds of formula I.2 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is H.

Table 87. Compounds of formula I.2 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is H.

Table 88. Compounds of formula I.2 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is H.

Table 89. Compounds of formula I.2 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is H.

Table 90. Compounds of formula I.2 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is H.

Table 91. Compounds of formula I.2 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is H.

Table 92. Compounds of formula I.2 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is H.

Table 93. Compounds of formula I.2 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is H.

Table 94. Compounds of formula I.2 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is H.

Table 95. Compounds of formula I.2 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is H.

Table 96. Compounds of formula I.2 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is H.

Table 97. Compounds of formula I.2 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is H.

Table 98. Compounds of formula I.2 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is H.

Table 99. Compounds of formula I.2 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is H.

Table 100. Compounds of formula I.2 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is H.

Table 101. Compounds of formula I.2 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is CH₃.

Table 102. Compounds of formula I.2 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is CH₃.

Table 103. Compounds of formula I.2 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is CH₃.

Table 104. Compounds of formula I.2 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is CH₃.

Table 105. Compounds of formula I.2 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is CH₃.

Table 106. Compounds of formula I.2 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is CH₃.

Table 107. Compounds of formula I.2 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is CH₃.

Table 108. Compounds of formula I.2 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is CH₃.

Table 109. Compounds of formula I.2 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is CH₃.

Table 110. Compounds of formula I.2 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is CH₃.

Table 111. Compounds of formula I.2 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is CH₃.

Table 112. Compounds of formula I.2 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is CH₃.

Table 113. Compounds of formula I.2 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is CH₃.

Table 114. Compounds of formula I.2 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is CH₃.

Table 115. Compounds of formula I.2 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is CH₃.

Table 116. Compounds of formula I.2 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is CH₃.

Table 117. Compounds of formula I.2 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is CH₃.

Table 118. Compounds of formula I.2 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is CH₃.

Table 119. Compounds of formula I.2 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is CH₃.

Table 120. Compounds of formula I.2 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is CH₃.

Table 121. Compounds of formula I.3 wherein R¹ is Y-1A, R⁴ is H and R⁵ is H.

Table 122. Compounds of formula I.3 wherein R¹ is Y-1B, R⁴ is H and R⁵ is H.

Table 123. Compounds of formula I.3 wherein R¹ is Y-2A, R⁴ is H and R⁵ is H.

Table 124. Compounds of formula I.3 wherein R¹ is Y-2B, R⁴ is H and R⁵ is H.

Table 125. Compounds of formula I.3 wherein R¹ is Y-3A, R⁴ is H and R⁵ is H.

Table 126. Compounds of formula I.3 wherein R¹ is Y-3B, R⁴ is H and R⁵ is H.

Table 127. Compounds of formula I.3 wherein R¹ is Y-3C, R⁴ is H and R⁵ is H.

Table 128. Compounds of formula I.3 wherein R¹ is Y-3D, R⁴ is H and R⁵ is H.

Table 129. Compounds of formula I.3 wherein R¹ is Y-4A, R⁴ is H and R⁵ is H.

Table 130. Compounds of formula I.3 wherein R¹ is Y-4B, R⁴ is H and R⁵ is H.

Table 131. Compounds of formula I.3 wherein R¹ is Y-40, R⁴ is H and R⁵ is H.

Table 132. Compounds of formula I.3 wherein R¹ is Y-4D, R⁴ is H and R⁵ is H.

Table 133. Compounds of formula I.3 wherein R¹ is Y-5A, R⁴ is H and R⁵ is H.

Table 134. Compounds of formula I.3 wherein R¹ is Y-5B, R⁴ is H and R⁵ is H.

Table 135. Compounds of formula I.3 wherein R¹ is Y-6A, R⁴ is H and R⁵ is H.

Table 136. Compounds of formula I.3 wherein R¹ is Y-6B, R⁴ is H and R⁵ is H.

Table 137. Compounds of formula I.3 wherein R¹ is Y-7A, R⁴ is H and R⁵ is H.

Table 138. Compounds of formula I.3 wherein R¹ is Y-7B, R⁴ is H and R⁵ is H.

Table 139. Compounds of formula I.3 wherein R¹ is Y-8A, R⁴ is H and R⁵ is H.

Table 140. Compounds of formula I.3 wherein R¹ is Y-8B, R⁴ is H and R⁵ is H.

Table 141. Compounds of formula I.3 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is H.

Table 142. Compounds of formula I.3 wherein R¹ is Y-1B, R⁴ is CH₃ and R⁵ is H.

Table 143. Compounds of formula I.3 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is H.

Table 144. Compounds of formula I.3 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is H.

Table 145. Compounds of formula I.3 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is H.

Table 146. Compounds of formula I.3 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is H.

Table 147. Compounds of formula I.3 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is H.

Table 148. Compounds of formula I.3 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is H.

Table 149. Compounds of formula I.3 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is H.

Table 150. Compounds of formula I.3 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is H.

Table 151. Compounds of formula I.3 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is H.

Table 152. Compounds of formula I.3 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is H.

Table 153. Compounds of formula I.3 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is H.

Table 154. Compounds of formula I.3 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is H.

Table 155. Compounds of formula I.3 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is H.

Table 156. Compounds of formula I.3 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is H.

Table 157. Compounds of formula I.3 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is H.

Table 158. Compounds of formula I.3 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is H.

Table 159. Compounds of formula I.3 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is H.

Table 160. Compounds of formula I.3 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is H.

Table 161. Compounds of formula I.3 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is CH₃.

Table 162. Compounds of formula I.3 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is CH₃.

Table 163. Compounds of formula I.3 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is CH₃.

Table 164. Compounds of formula I.3 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is CH₃.

Table 165. Compounds of formula I.3 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is CH₃.

Table 166. Compounds of formula I.3 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is CH₃.

Table 167. Compounds of formula I.3 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is CH₃.

Table 168. Compounds of formula I.3 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is CH₃.

Table 169. Compounds of formula I.3 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is CH₃.

Table 170. Compounds of formula I.3 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is CH₃.

Table 171. Compounds of formula I.3 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is CH₃.

Table 172. Compounds of formula I.3 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is CH₃.

Table 173. Compounds of formula I.3 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is CH₃.

Table 174. Compounds of formula I.3 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is CH₃.

Table 175. Compounds of formula I.3 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is CH₃.

Table 176. Compounds of formula I.3 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is CH₃.

Table 177. Compounds of formula I.3 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is CH₃.

Table 178. Compounds of formula I.3 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is CH₃.

Table 179. Compounds of formula I.3 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is CH₃.

Table 180. Compounds of formula I.3 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is CH₃.

Table 181. Compounds of formula I.4 wherein R¹ is Y-1A, R⁴ is H and R⁵ is H.

Table 182. Compounds of formula I.4 wherein R¹ is Y-1 B, R⁴ is H and R⁵ is H.

Table 183. Compounds of formula I.4 wherein R¹ is Y-2A, R⁴ is H and R⁵ is H.

Table 184. Compounds of formula I.4 wherein R¹ is Y-2B, R⁴ is H and R⁵ is H.

Table 185. Compounds of formula I.4 wherein R¹ is Y-3A, R⁴ is H and R⁵ is H.

Table 186. Compounds of formula I.4 wherein R¹ is Y-3B, R⁴ is H and R⁵ is H.

Table 187. Compounds of formula I.4 wherein R¹ is Y-3C, R⁴ is H and R⁵ is H.

Table 188. Compounds of formula I.4 wherein R¹ is Y-3D, R⁴ is H and R⁵ is H.

Table 189. Compounds of formula I.4 wherein R¹ is Y-4A, R⁴ is H and R⁵ is H.

Table 190. Compounds of formula I.4 wherein R¹ is Y-4B, R⁴ is H and R⁵ is H.

Table 191. Compounds of formula I.4 wherein R¹ is Y-4C, R⁴ is H and R⁵ is H.

Table 192. Compounds of formula I.4 wherein R¹ is Y-4D, R⁴ is H and R⁵ is H.

Table 193. Compounds of formula I.4 wherein R¹ is Y-5A, R⁴ is H and R⁵ is H.

Table 194. Compounds of formula I.4 wherein R¹ is Y-5B, R⁴ is H and R⁵ is H.

Table 195. Compounds of formula I.4 wherein R¹ is Y-6A, R⁴ is H and R⁵ is H.

Table 196. Compounds of formula I.4 wherein R¹ is Y-6B, R⁴ is H and R⁵ is H.

Table 197. Compounds of formula I.4 wherein R¹ is Y-7A, R⁴ is H and R⁵ is H.

Table 198. Compounds of formula I.4 wherein R¹ is Y-7B, R⁴ is H and R⁵ is H.

Table 199. Compounds of formula I.4 wherein R¹ is Y-8A, R⁴ is H and R⁵ is H.

Table 200. Compounds of formula I.4 wherein R¹ is Y-8B, R⁴ is H and R⁵ is H.

Table 201. Compounds of formula I.4 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is H.

Table 202. Compounds of formula I.4 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is H.

Table 203. Compounds of formula I.4 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is H.

Table 204. Compounds of formula I.4 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is H.

Table 205. Compounds of formula I.4 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is H.

Table 206. Compounds of formula I.4 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is H.

Table 207. Compounds of formula I.4 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is H.

Table 208. Compounds of formula I.4 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is H.

Table 209. Compounds of formula I.4 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is H.

Table 210. Compounds of formula I.4 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is H.

Table 211. Compounds of formula I.4 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is H.

Table 212. Compounds of formula I.4 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is H.

Table 213. Compounds of formula I.4 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is H.

Table 214. Compounds of formula I.4 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is H.

Table 215. Compounds of formula I.4 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is H.

Table 216. Compounds of formula I.4 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is H.

Table 217. Compounds of formula I.4 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is H.

Table 218. Compounds of formula I.4 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is H.

Table 219. Compounds of formula I.4 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is H.

Table 220. Compounds of formula I.4 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is H.

Table 221. Compounds of formula I.4 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is CH₃.

Table 222. Compounds of formula I.4 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is CH₃.

Table 223. Compounds of formula I.4 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is CH₃.

Table 224. Compounds of formula I.4 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is CH₃.

Table 225. Compounds of formula I.4 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is CH₃.

Table 226. Compounds of formula I.4 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is CH₃.

Table 227. Compounds of formula I.4 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is CH₃.

Table 228. Compounds of formula I.4 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is CH₃.

Table 229. Compounds of formula I.4 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is CH₃.

Table 230. Compounds of formula I.4 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is CH₃.

Table 231. Compounds of formula I.4 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is CH₃.

Table 232. Compounds of formula I.4 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is CH₃.

Table 233. Compounds of formula I.4 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is CH₃.

Table 234. Compounds of formula I.4 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is CH₃.

Table 235. Compounds of formula I.4 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is CH₃.

Table 236. Compounds of formula I.4 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is CH₃.

Table 237. Compounds of formula I.4 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is CH₃.

Table 238. Compounds of formula I.4 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is CH₃.

Table 239. Compounds of formula I.4 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is CH₃.

Table 240. Compounds of formula I.4 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is CH₃.

Table 241. Compounds of formula I.5 wherein R¹ is Y-1A, R⁴ is H and R⁵ is H.

Table 242. Compounds of formula I.5 wherein R¹ is Y-1 B, R⁴ is H and R⁵ is H.

Table 243. Compounds of formula I.5 wherein R¹ is Y-2A, R⁴ is H and R⁵ is H.

Table 244. Compounds of formula I.5 wherein R¹ is Y-2B, R⁴ is H and R⁵ is H.

Table 245. Compounds of formula I.5 wherein R¹ is Y-3A, R⁴ is H and R⁵ is H.

Table 246. Compounds of formula I.5 wherein R¹ is Y-3B, R⁴ is H and R⁵ is H.

Table 247. Compounds of formula I.5 wherein R¹ is Y-3C, R⁴ is H and R⁵ is H.

Table 248. Compounds of formula I.5 wherein R¹ is Y-3D, R⁴ is H and R⁵ is H.

Table 249. Compounds of formula I.5 wherein R¹ is Y-4A, R⁴ is H and R⁵ is H.

Table 250. Compounds of formula I.5 wherein R¹ is Y-4B, R⁴ is H and R⁵ is H.

Table 251. Compounds of formula I.5 wherein R¹ is Y-4C, R⁴ is H and R⁵ is H.

Table 252. Compounds of formula I.5 wherein R¹ is Y-4D, R⁴ is H and R⁵ is H.

Table 253. Compounds of formula I.5 wherein R¹ is Y-5A, R⁴ is H and R⁵ is H.

Table 254. Compounds of formula I.5 wherein R¹ is Y-5B, R⁴ is H and R⁵ is H.

Table 255. Compounds of formula I.5 wherein R¹ is Y-6A, R⁴ is H and R⁵ is H.

Table 256. Compounds of formula I.5 wherein R¹ is Y-6B, R⁴ is H and R⁵ is H.

Table 257. Compounds of formula I.5 wherein R¹ is Y-7A, R⁴ is H and R⁵ is H.

Table 258. Compounds of formula I.5 wherein R¹ is Y-7B, R⁴ is H and R⁵ is H.

Table 259. Compounds of formula I.5 wherein R¹ is Y-8A, R⁴ is H and R⁵ is H.

Table 260. Compounds of formula I.5 wherein R¹ is Y-8B, R⁴ is H and R⁵ is H.

Table 261. Compounds of formula I.5 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is H.

Table 262. Compounds of formula I.5 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is H.

Table 263. Compounds of formula I.5 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is H.

Table 264. Compounds of formula I.5 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is H.

Table 265. Compounds of formula I.5 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is H.

Table 266. Compounds of formula I.5 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is H.

Table 267. Compounds of formula I.5 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is H.

Table 268. Compounds of formula I.5 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is H.

Table 269. Compounds of formula I.5 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is H.

Table 270. Compounds of formula I.5 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is H.

Table 271. Compounds of formula I.5 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is H.

Table 272. Compounds of formula I.5 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is H.

Table 273. Compounds of formula I.5 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is H.

Table 274. Compounds of formula I.5 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is H.

Table 275. Compounds of formula I.5 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is H.

Table 276. Compounds of formula I.5 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is H.

Table 277. Compounds of formula I.5 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is H.

Table 278. Compounds of formula I.5 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is H.

Table 279. Compounds of formula I.5 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is H.

Table 280. Compounds of formula I.5 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is H.

Table 281. Compounds of formula I.5 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is CH₃.

Table 282. Compounds of formula I.5 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is CH₃.

Table 283. Compounds of formula I.5 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is CH₃.

Table 284. Compounds of formula I.5 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is CH₃.

Table 285. Compounds of formula I.5 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is CH₃.

Table 286. Compounds of formula I.5 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is CH₃.

Table 287. Compounds of formula I.5 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is CH₃.

Table 288. Compounds of formula I.5 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is CH₃.

Table 289. Compounds of formula I.5 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is CH₃.

Table 290. Compounds of formula I.5 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is CH₃.

Table 291. Compounds of formula I.5 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is CH₃.

Table 292. Compounds of formula I.5 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is CH₃.

Table 293. Compounds of formula I.5 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is CH₃.

Table 294. Compounds of formula I.5 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is CH₃.

Table 295. Compounds of formula I.5 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is CH₃.

Table 296. Compounds of formula I.5 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is CH₃.

Table 297. Compounds of formula I.5 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is CH₃.

Table 298. Compounds of formula I.5 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is CH₃.

Table 299. Compounds of formula I.5 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is CH₃.

Table 300. Compounds of formula I.5 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is CH₃.

Table 301. Compounds of formula I.6 wherein R¹ is Y-1A, R⁴ is H and R⁵ is H.

Table 302. Compounds of formula I.6 wherein R¹ is Y-1 B, R⁴ is H and R⁵ is H.

Table 303. Compounds of formula I.6 wherein R¹ is Y-2A, R⁴ is H and R⁵ is H.

Table 304. Compounds of formula I.6 wherein R¹ is Y-2B, R⁴ is H and R⁵ is H.

Table 305. Compounds of formula I.6 wherein R¹ is Y-3A, R⁴ is H and R⁵ is H.

Table 306. Compounds of formula I.6 wherein R¹ is Y-3B, R⁴ is H and R⁵ is H.

Table 307. Compounds of formula I.6 wherein R¹ is Y-3C, R⁴ is H and R⁵ is H.

Table 308. Compounds of formula I.6 wherein R¹ is Y-3D, R⁴ is H and R⁵ is H.

Table 309. Compounds of formula I.6 wherein R¹ is Y-4A, R⁴ is H and R⁵ is H.

Table 310. Compounds of formula I.6 wherein R¹ is Y-4B, R⁴ is H and R⁵ is H.

Table 311. Compounds of formula I.6 wherein R¹ is Y-4C, R⁴ is H and R⁵ is H.

Table 312. Compounds of formula I.6 wherein R¹ is Y-4D, R⁴ is H and R⁵ is H.

Table 313. Compounds of formula I.6 wherein R¹ is Y-5A, R⁴ is H and R⁵ is H.

Table 314. Compounds of formula I.6 wherein R¹ is Y-5B, R⁴ is H and R⁵ is H.

Table 315. Compounds of formula I.6 wherein R¹ is Y-6A, R⁴ is H and R⁵ is H.

Table 316. Compounds of formula I.6 wherein R¹ is Y-6B, R⁴ is H and R⁵ is H.

Table 317. Compounds of formula I.6 wherein R¹ is Y-7A, R⁴ is H and R⁵ is H.

Table 318. Compounds of formula I.6 wherein R¹ is Y-7B, R⁴ is H and R⁵ is H.

Table 319. Compounds of formula I.6 wherein R¹ is Y-8A, R⁴ is H and R⁵ is H.

Table 320. Compounds of formula I.6 wherein R¹ is Y-8B, R⁴ is H and R⁵ is H.

Table 321. Compounds of formula I.6 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is H.

Table 322. Compounds of formula I.6 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is H.

Table 323. Compounds of formula I.6 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is H.

Table 324. Compounds of formula I.6 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is H.

Table 325. Compounds of formula I.6 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is H.

Table 326. Compounds of formula I.6 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is H.

Table 327. Compounds of formula I.6 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is H.

Table 328. Compounds of formula I.6 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is H.

Table 329. Compounds of formula I.6 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is H.

Table 330. Compounds of formula I.6 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is H.

Table 331. Compounds of formula I.6 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is H.

Table 332. Compounds of formula I.6 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is H.

Table 333. Compounds of formula I.6 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is H.

Table 334. Compounds of formula I.6 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is H.

Table 335. Compounds of formula I.6 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is H.

Table 336. Compounds of formula I.6 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is H.

Table 337. Compounds of formula I.6 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is H.

Table 338. Compounds of formula I.6 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is H.

Table 339. Compounds of formula I.6 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is H.

Table 340. Compounds of formula I.6 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is H.

Table 341. Compounds of formula I.6 wherein R¹ is Y-1A, R⁴ is CH₃ and R⁵ is CH₃.

Table 342. Compounds of formula I.6 wherein R¹ is Y-1 B, R⁴ is CH₃ and R⁵ is CH₃.

Table 343. Compounds of formula I.6 wherein R¹ is Y-2A, R⁴ is CH₃ and R⁵ is CH₃.

Table 344. Compounds of formula I.6 wherein R¹ is Y-2B, R⁴ is CH₃ and R⁵ is CH₃.

Table 345. Compounds of formula I.6 wherein R¹ is Y-3A, R⁴ is CH₃ and R⁵ is CH₃.

Table 346. Compounds of formula I.6 wherein R¹ is Y-3B, R⁴ is CH₃ and R⁵ is CH₃.

Table 347. Compounds of formula I.6 wherein R¹ is Y-3C, R⁴ is CH₃ and R⁵ is CH₃.

Table 348. Compounds of formula I.6 wherein R¹ is Y-3D, R⁴ is CH₃ and R⁵ is CH₃.

Table 349. Compounds of formula I.6 wherein R¹ is Y-4A, R⁴ is CH₃ and R⁵ is CH₃.

Table 350. Compounds of formula I.6 wherein R¹ is Y-4B, R⁴ is CH₃ and R⁵ is CH₃.

Table 351. Compounds of formula I.6 wherein R¹ is Y-4C, R⁴ is CH₃ and R⁵ is CH₃.

Table 352. Compounds of formula I.6 wherein R¹ is Y-4D, R⁴ is CH₃ and R⁵ is CH₃.

Table 353. Compounds of formula I.6 wherein R¹ is Y-5A, R⁴ is CH₃ and R⁵ is CH₃.

Table 354. Compounds of formula I.6 wherein R¹ is Y-5B, R⁴ is CH₃ and R⁵ is CH₃.

Table 355. Compounds of formula I.6 wherein R¹ is Y-6A, R⁴ is CH₃ and R⁵ is CH₃.

Table 356. Compounds of formula I.6 wherein R¹ is Y-6B, R⁴ is CH₃ and R⁵ is CH₃.

Table 357. Compounds of formula I.6 wherein R¹ is Y-7A, R⁴ is CH₃ and R⁵ is CH₃.

Table 358. Compounds of formula I.6 wherein R¹ is Y-7B, R⁴ is CH₃ and R⁵ is CH₃.

Table 359. Compounds of formula I.6 wherein R¹ is Y-8A, R⁴ is CH₃ and R⁵ is CH₃.

Table 360. Compounds of formula I.6 wherein R¹ is Y-8B, R⁴ is CH₃ and R⁵ is CH₃.

Table 361. Compounds of formula I.7 wherein R¹ is Y-1A, R² is H, R⁹ is H and R¹⁰ is H.

Table 362. Compounds of formula I.7 wherein R¹ is Y-1A, R² is H, R⁹ is CH₃ and, R¹⁰ is H.

Table 363. Compounds of formula I.7 wherein R¹ is Y-1A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 364. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is H, R⁹ is H and R¹⁰ is H.

Table 365. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 366. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 367. Compounds of formula I.7 wherein R¹ is Y-2A, R² is H, R⁹ is H and R¹⁰ is H.

Table 368. Compounds of formula I.7 wherein R¹ is Y-2A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 369. Compounds of formula I.7 wherein R¹ is Y-2A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 370. Compounds of formula I.7 wherein R¹ is Y-2B, R² is H, R⁹ is H and R¹⁰ is H.

Table 371. Compounds of formula I.7 wherein R¹ is Y-2B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 372. Compounds of formula I.7 wherein R¹ is Y-2B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 373. Compounds of formula I.7 wherein R¹ is Y-3A, R² is H, R⁹ is H and R¹⁰ is H.

Table 374. Compounds of formula I.7 wherein R¹ is Y-3A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 375. Compounds of formula I.7 wherein R¹ is Y-3A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 376. Compounds of formula I.7 wherein R¹ is Y-3B, R² is H, R⁹ is H and R¹⁰ is H.

Table 377. Compounds of formula I.7 wherein R¹ is Y-3B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 378. Compounds of formula I.7 wherein R¹ is Y-3B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 379. Compounds of formula I.7 wherein R¹ is Y-3C, R² is H, R⁹ is H and R¹⁰ is H.

Table 380. Compounds of formula I.7 wherein R¹ is Y-3C, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 381. Compounds of formula I.7 wherein R¹ is Y-3C, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 382. Compounds of formula I.7 wherein R¹ is Y-3D, R² is H, R⁹ is H and R¹⁰ is H.

Table 383. Compounds of formula I.7 wherein R¹ is Y-3D, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 384. Compounds of formula I.7 wherein R¹ is Y-3D, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 385. Compounds of formula I.7 wherein R¹ is Y-4A, R² is H, R⁹ is H and R¹⁰ is H.

Table 386. Compounds of formula I.7 wherein R¹ is Y-4A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 387. Compounds of formula I.7 wherein R¹ is Y-4A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 388. Compounds of formula I.7 wherein R¹ is Y-4B, R² is H, R⁹ is H and R¹⁰ is H.

Table 389. Compounds of formula I.7 wherein R¹ is Y-4B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 390. Compounds of formula I.7 wherein R¹ is Y-4B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 391. Compounds of formula I.7 wherein R¹ is Y-4C, R² is H, R⁹ is H and R¹⁰ is H.

Table 392. Compounds of formula I.7 wherein R¹ is Y-4C, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 393. Compounds of formula I.7 wherein R¹ is Y-4C, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 394. Compounds of formula I.7 wherein R¹ is Y-4D, R² is H, R⁹ is H and R¹⁰ is H.

Table 395. Compounds of formula I.7 wherein R¹ is Y-4D, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 396. Compounds of formula I.7 wherein R¹ is Y-4D, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 397. Compounds of formula I.7 wherein R¹ is Y-5A, R² is H, R⁹ is H and R¹⁰ is H.

Table 398. Compounds of formula I.7 wherein R¹ is Y-5A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 399. Compounds of formula I.7 wherein R¹ is Y-5A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 400. Compounds of formula I.7 wherein R¹ is Y-5B, R² is H, R⁹ is H and R¹⁰ is H.

Table 401. Compounds of formula I.7 wherein R¹ is Y-5B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 402. Compounds of formula I.7 wherein R¹ is Y-5B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 403. Compounds of formula I.7 wherein R¹ is Y-6A, R² is H, R⁹ is H and R¹⁰ is H.

Table 404. Compounds of formula I.7 wherein R¹ is Y-6A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 405. Compounds of formula I.7 wherein R¹ is Y-6A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 406. Compounds of formula I.7 wherein R¹ is Y-6B, R² is H, R⁹ is H and R¹⁰ is H.

Table 407. Compounds of formula I.7 wherein R¹ is Y-6B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 408. Compounds of formula I.7 wherein R¹ is Y-6B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 409. Compounds of formula I.7 wherein R¹ is Y-7A, R² is H, R⁹ is H and R¹⁰ is H.

Table 410. Compounds of formula I.7 wherein R¹ is Y-7A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 411. Compounds of formula I.7 wherein R¹ is Y-7A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 412. Compounds of formula I.7 wherein R¹ is Y-7B, R² is H, R⁹ is H and R¹⁰ is H.

Table 413. Compounds of formula I.7 wherein R¹ is Y-7B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 414. Compounds of formula I.7 wherein R¹ is Y-7B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 415. Compounds of formula I.7 wherein R¹ is Y-8A, R² is H, R⁹ is H and R¹⁰ is H.

Table 416. Compounds of formula I.7 wherein R¹ is Y-8A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 417. Compounds of formula I.7 wherein R¹ is Y-8A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 418. Compounds of formula I.7 wherein R¹ is Y-8B, R² is H, R⁹ is H and R¹⁰ is H.

Table 419. Compounds of formula I.7 wherein R¹ is Y-8B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 420. Compounds of formula I.7 wherein R¹ is Y-8B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 421. Compounds of formula I.7 wherein R¹ is Y-1A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 422. Compounds of formula I.7 wherein R¹ is Y-1A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 423. Compounds of formula I.7 wherein R¹ is Y-1A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 424. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 425. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 426. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 427. Compounds of formula I.7 wherein R¹ is Y-2A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 428. Compounds of formula I.7 wherein R¹ is Y-2A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 429. Compounds of formula I.7 wherein R¹ is Y-2A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 430. Compounds of formula I.7 wherein R¹ is Y-2B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 431. Compounds of formula I.7 wherein R¹ is Y-2B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 432. Compounds of formula I.7 wherein R¹ is Y-2B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 433. Compounds of formula I.7 wherein R¹ is Y-3A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 434. Compounds of formula I.7 wherein R¹ is Y-3A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 435. Compounds of formula I.7 wherein R¹ is Y-3A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 436. Compounds of formula I.7 wherein R¹ is Y-3B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 437. Compounds of formula I.7 wherein R¹ is Y-3B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 438. Compounds of formula I.7 wherein R¹ is Y-3B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 439. Compounds of formula I.7 wherein R¹ is Y-3C, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 440. Compounds of formula I.7 wherein R¹ is Y-3C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 441. Compounds of formula I.7 wherein R¹ is Y-3C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 442. Compounds of formula I.7 wherein R¹ is Y-3D, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 443. Compounds of formula I.7 wherein R¹ is Y-3D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 444. Compounds of formula I.7 wherein R¹ is Y-3D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 445. Compounds of formula I.7 wherein R¹ is Y-4A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 446. Compounds of formula I.7 wherein R¹ is Y-4A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 447. Compounds of formula I.7 wherein R¹ is Y-4A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 448. Compounds of formula I.7 wherein R¹ is Y-4B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 449. Compounds of formula I.7 wherein R¹ is Y-4B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 450. Compounds of formula I.7 wherein R¹ is Y-4B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 451. Compounds of formula I.7 wherein R¹ is Y-4C, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 452. Compounds of formula I.7 wherein R¹ is Y-4C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 453. Compounds of formula I.7 wherein R¹ is Y-4C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 454. Compounds of formula I.7 wherein R¹ is Y-4D, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 455. Compounds of formula I.7 wherein R¹ is Y-4D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 456. Compounds of formula I.7 wherein R¹ is Y-4D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 457. Compounds of formula I.7 wherein R¹ is Y-5A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 458. Compounds of formula I.7 wherein R¹ is Y-5A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 459. Compounds of formula I.7 wherein R¹ is Y-5A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 460. Compounds of formula I.7 wherein R¹ is Y-5B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 461. Compounds of formula I.7 wherein R¹ is Y-5B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 462. Compounds of formula I.7 wherein R¹ is Y-5B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 463. Compounds of formula I.7 wherein R¹ is Y-6A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 464. Compounds of formula I.7 wherein R¹ is Y-6A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 465. Compounds of formula I.7 wherein R¹ is Y-6A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 466. Compounds of formula I.7 wherein R¹ is Y-6B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 467. Compounds of formula I.7 wherein R¹ is Y-6B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 468. Compounds of formula I.7 wherein R¹ is Y-6B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 469. Compounds of formula I.7 wherein R¹ is Y-7A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 470. Compounds of formula I.7 wherein R¹ is Y-7A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 471. Compounds of formula I.7 wherein R¹ is Y-7A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 472. Compounds of formula I.7 wherein R¹ is Y-7B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 473. Compounds of formula I.7 wherein R¹ is Y-7B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 474. Compounds of formula I.7 wherein R¹ is Y-7B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 475. Compounds of formula I.7 wherein R¹ is Y-8A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 476. Compounds of formula I.7 wherein R¹ is Y-8A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 477. Compounds of formula I.7 wherein R¹ is Y-8A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 478. Compounds of formula I.7 wherein R¹ is Y-8B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 479. Compounds of formula I.7 wherein R¹ is Y-8B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 480. Compounds of formula I.7 wherein R¹ is Y-8B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 481. Compounds of formula I.7 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 482. Compounds of formula I.7 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 483. Compounds of formula I.7 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 484. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 485. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 486. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 487. Compounds of formula I.7 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 488. Compounds of formula I.7 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 489. Compounds of formula I.7 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 490. Compounds of formula I.7 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 491. Compounds of formula I.7 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 492. Compounds of formula I.7 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 493. Compounds of formula I.7 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 494. Compounds of formula I.7 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 495. Compounds of formula I.7 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 496. Compounds of formula I.7 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 497. Compounds of formula I.7 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 498. Compounds of formula I.7 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 499. Compounds of formula I.7 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 500. Compounds of formula I.7 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 501. Compounds of formula I.7 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 502. Compounds of formula I.7 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 503. Compounds of formula I.7 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 504. Compounds of formula I.7 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 505. Compounds of formula I.7 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 506. Compounds of formula I.7 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 507. Compounds of formula I.7 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 508. Compounds of formula I.7 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 509. Compounds of formula I.7 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 510. Compounds of formula I.7 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 511. Compounds of formula I.7 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 512. Compounds of formula I.7 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 513. Compounds of formula I.7 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 514. Compounds of formula I.7 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 515. Compounds of formula I.7 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 516. Compounds of formula I.7 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 517. Compounds of formula I.7 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 518. Compounds of formula I.7 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 519. Compounds of formula I.7 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 520. Compounds of formula I.7 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 521. Compounds of formula I.7 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 522. Compounds of formula I.7 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 523. Compounds of formula I.7 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 524. Compounds of formula I.7 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 525. Compounds of formula I.7 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 526. Compounds of formula I.7 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 527. Compounds of formula I.7 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 528. Compounds of formula I.7 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 529. Compounds of formula I.7 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 530. Compounds of formula I.7 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 531. Compounds of formula I.7 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 532. Compounds of formula I.7 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 533. Compounds of formula I.7 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 534. Compounds of formula I.7 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 535. Compounds of formula I.7 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 536. Compounds of formula I.7 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 537. Compounds of formula I.7 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 538. Compounds of formula I.7 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 539. Compounds of formula I.7 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 540. Compounds of formula I.7 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 541. Compounds of formula I.7 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 542. Compounds of formula I.7 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 543. Compounds of formula I.7 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 544. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 545. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is c-C₃H₅, R⁹ is CH₃, R¹⁰ is H.

Table 546. Compounds of formula I.7 wherein R¹ is Y-1 B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 547. Compounds of formula I.7 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 548. Compounds of formula I.7 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 549. Compounds of formula I.7 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 550. Compounds of formula I.7 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 551. Compounds of formula I.7 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 552. Compounds of formula I.7 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 553. Compounds of formula I.7 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 554. Compounds of formula I.7 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 555. Compounds of formula I.7 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 556. Compounds of formula I.7 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 557. Compounds of formula I.7 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 558. Compounds of formula I.7 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 559. Compounds of formula I.7 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 560. Compounds of formula I.7 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 561. Compounds of formula I.7 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 562. Compounds of formula I.7 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 563. Compounds of formula I.7 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 564. Compounds of formula I.7 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 565. Compounds of formula I.7 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 566. Compounds of formula I.7 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 567. Compounds of formula I.7 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 568. Compounds of formula I.7 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 569. Compounds of formula I.7 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 570. Compounds of formula I.7 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 571. Compounds of formula I.7 wherein R¹ is Y-4C, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 572. Compounds of formula I.7 wherein R¹ is Y-4C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 573. Compounds of formula I.7 wherein R¹ is Y-4C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 574. Compounds of formula I.7 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 575. Compounds of formula I.7 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 576. Compounds of formula I.7 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 577. Compounds of formula I.7 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 578. Compounds of formula I.7 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 579. Compounds of formula I.7 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 580. Compounds of formula I.7 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 581. Compounds of formula I.7 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 582. Compounds of formula I.7 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 583. Compounds of formula I.7 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 584. Compounds of formula I.7 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 585. Compounds of formula I.7 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 586. Compounds of formula I.7 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 587. Compounds of formula I.7 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 588. Compounds of formula I.7 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 589. Compounds of formula I.7 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 590. Compounds of formula I.7 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 591. Compounds of formula I.7 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 592. Compounds of formula I.7 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 593. Compounds of formula I.7 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 594. Compounds of formula I.7 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 595. Compounds of formula I.7 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 596. Compounds of formula I.7 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 597. Compounds of formula I.7 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 598. Compounds of formula I.7 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 599. Compounds of formula I.7 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 600. Compounds of formula I.7 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 601. Compounds of formula I.8 wherein R¹ is Y-1A, R² is H, R⁹ is H and R¹⁰ is H.

Table 602. Compounds of formula I.8 wherein R¹ is Y-1A, R² is H, R⁹ is CH₃ and, R¹⁰ is H.

Table 603. Compounds of formula I.8 wherein R¹ is Y-1A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 604. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is H, R⁹ is H and R¹⁰ is H.

Table 605. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 606. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 607. Compounds of formula I.8 wherein R¹ is Y-2A, R² is H, R⁹ is H and R¹⁰ is H.

Table 608. Compounds of formula I.8 wherein R¹ is Y-2A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 609. Compounds of formula I.8 wherein R¹ is Y-2A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 610. Compounds of formula I.8 wherein R¹ is Y-2B, R² is H, R⁹ is H and R¹⁰ is H.

Table 611. Compounds of formula I.8 wherein R¹ is Y-2B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 612. Compounds of formula I.8 wherein R¹ is Y-2B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 613. Compounds of formula I.8 wherein R¹ is Y-3A, R² is H, R⁹ is H and R¹⁰ is H.

Table 614. Compounds of formula I.8 wherein R¹ is Y-3A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 615. Compounds of formula I.8 wherein R¹ is Y-3A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 616. Compounds of formula I.8 wherein R¹ is Y-3B, R² is H, R⁹ is H and R¹⁰ is H.

Table 617. Compounds of formula I.8 wherein R¹ is Y-3B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 618. Compounds of formula I.8 wherein R¹ is Y-3B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 619. Compounds of formula I.8 wherein R¹ is Y-3C, R² is H, R⁹ is H and R¹⁰ is H.

Table 620. Compounds of formula I.8 wherein R¹ is Y-3C, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 621. Compounds of formula I.8 wherein R¹ is Y-3C, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 622. Compounds of formula I.8 wherein R¹ is Y-3D, R² is H, R⁹ is H and R¹⁰ is H.

Table 623. Compounds of formula I.8 wherein R¹ is Y-3D, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 624. Compounds of formula I.8 wherein R¹ is Y-3D, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 625. Compounds of formula I.8 wherein R¹ is Y-4A, R² is H, R⁹ is H and R¹⁰ is H.

Table 626. Compounds of formula I.8 wherein R¹ is Y-4A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 627. Compounds of formula I.8 wherein R¹ is Y-4A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 628. Compounds of formula I.8 wherein R¹ is Y-4B, R² is H, R⁹ is H and R¹⁰ is H.

Table 629. Compounds of formula I.8 wherein R¹ is Y-4B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 630. Compounds of formula I.8 wherein R¹ is Y-4B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 631. Compounds of formula I.8 wherein R¹ is Y-4C, R² is H, R⁹ is H and R¹⁰ is H.

Table 632. Compounds of formula I.8 wherein R¹ is Y-4C, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 633. Compounds of formula I.8 wherein R¹ is Y-4C, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 634. Compounds of formula I.8 wherein R¹ is Y-4D, R² is H, R⁹ is H and R¹⁰ is H.

Table 635. Compounds of formula I.8 wherein R¹ is Y-4D, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 636. Compounds of formula I.8 wherein R¹ is Y-4D, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 637. Compounds of formula I.8 wherein R¹ is Y-5A, R² is H, R⁹ is H and R¹⁰ is H.

Table 638. Compounds of formula I.8 wherein R¹ is Y-5A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 639. Compounds of formula I.8 wherein R¹ is Y-5A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 640. Compounds of formula I.8 wherein R¹ is Y-5B, R² is H, R⁹ is H and R¹⁰ is H.

Table 641. Compounds of formula I.8 wherein R¹ is Y-5B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 642. Compounds of formula I.8 wherein R¹ is Y-5B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 643. Compounds of formula I.8 wherein R¹ is Y-6A, R² is H, R⁹ is H and R¹⁰ is H.

Table 644. Compounds of formula I.8 wherein R¹ is Y-6A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 645. Compounds of formula I.8 wherein R¹ is Y-6A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 646. Compounds of formula I.8 wherein R¹ is Y-6B, R² is H, R⁹ is H and R¹⁰ is H.

Table 647. Compounds of formula I.8 wherein R¹ is Y-6B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 648. Compounds of formula I.8 wherein R¹ is Y-6B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 649. Compounds of formula I.8 wherein R¹ is Y-7A, R² is H, R⁹ is H and R¹⁰ is H.

Table 650. Compounds of formula I.8 wherein R¹ is Y-7A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 651. Compounds of formula I.8 wherein R¹ is Y-7A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 652. Compounds of formula I.8 wherein R¹ is Y-7B, R² is H, R⁹ is H and R¹⁰ is H.

Table 653. Compounds of formula I.8 wherein R¹ is Y-7B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 654. Compounds of formula I.8 wherein R¹ is Y-7B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 655. Compounds of formula I.8 wherein R¹ is Y-8A, R² is H, R⁹ is H and R¹⁰ is H.

Table 656. Compounds of formula I.8 wherein R¹ is Y-8A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 657. Compounds of formula I.8 wherein R¹ is Y-8A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 658. Compounds of formula I.8 wherein R¹ is Y-8B, R² is H, R⁹ is H and R¹⁰ is H.

Table 659. Compounds of formula I.8 wherein R¹ is Y-8B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 660. Compounds of formula I.8 wherein R¹ is Y-8B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 661. Compounds of formula I.8 wherein R¹ is Y-1A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 662. Compounds of formula I.8 wherein R¹ is Y-1A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 663. Compounds of formula I.8 wherein R¹ is Y-1A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 664. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 665. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 666. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 667. Compounds of formula I.8 wherein R¹ is Y-2A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 668. Compounds of formula I.8 wherein R¹ is Y-2A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 669. Compounds of formula I.8 wherein R¹ is Y-2A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 670. Compounds of formula I.8 wherein R¹ is Y-2B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 671. Compounds of formula I.8 wherein R¹ is Y-2B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 672. Compounds of formula I.8 wherein R¹ is Y-2B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 673. Compounds of formula I.8 wherein R¹ is Y-3A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 674. Compounds of formula I.8 wherein R¹ is Y-3A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 675. Compounds of formula I.8 wherein R¹ is Y-3A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 676. Compounds of formula I.8 wherein R¹ is Y-3B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 677. Compounds of formula I.8 wherein R¹ is Y-3B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 678. Compounds of formula I.8 wherein R¹ is Y-3B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 679. Compounds of formula I.8 wherein R¹ is Y-3C, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 680. Compounds of formula I.8 wherein R¹ is Y-3C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 681. Compounds of formula I.8 wherein R¹ is Y-3C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 682. Compounds of formula I.8 wherein R¹ is Y-3D, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 683. Compounds of formula I.8 wherein R¹ is Y-3D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 684. Compounds of formula I.8 wherein R¹ is Y-3D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 685. Compounds of formula I.8 wherein R¹ is Y-4A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 686. Compounds of formula I.8 wherein R¹ is Y-4A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 687. Compounds of formula I.8 wherein R¹ is Y-4A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 688. Compounds of formula I.8 wherein R¹ is Y-4B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 689. Compounds of formula I.8 wherein R¹ is Y-4B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 690. Compounds of formula I.8 wherein R¹ is Y-4B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 691. Compounds of formula I.8 wherein R¹ is Y-4C, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 692. Compounds of formula I.8 wherein R¹ is Y-4C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 693. Compounds of formula I.8 wherein R¹ is Y-40, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 694. Compounds of formula I.8 wherein R¹ is Y-4D, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 695. Compounds of formula I.8 wherein R¹ is Y-4D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 696. Compounds of formula I.8 wherein R¹ is Y-4D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 697. Compounds of formula I.8 wherein R¹ is Y-5A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 698. Compounds of formula I.8 wherein R¹ is Y-5A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 699. Compounds of formula I.8 wherein R¹ is Y-5A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 700. Compounds of formula I.8 wherein R¹ is Y-5B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 701. Compounds of formula I.8 wherein R¹ is Y-5B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 702. Compounds of formula I.8 wherein R¹ is Y-5B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 703. Compounds of formula I.8 wherein R¹ is Y-6A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 704. Compounds of formula I.8 wherein R¹ is Y-6A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 705. Compounds of formula I.8 wherein R¹ is Y-6A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 706. Compounds of formula I.8 wherein R¹ is Y-6B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 707. Compounds of formula I.8 wherein R¹ is Y-6B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 708. Compounds of formula I.8 wherein R¹ is Y-6B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 709. Compounds of formula I.8 wherein R¹ is Y-7A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 710. Compounds of formula I.8 wherein R¹ is Y-7A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 711. Compounds of formula I.8 wherein R¹ is Y-7A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 712. Compounds of formula I.8 wherein R¹ is Y-7B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 713. Compounds of formula I.8 wherein R¹ is Y-7B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 714. Compounds of formula I.8 wherein R¹ is Y-7B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 715. Compounds of formula I.8 wherein R¹ is Y-8A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 716. Compounds of formula I.8 wherein R¹ is Y-8A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 717. Compounds of formula I.8 wherein R¹ is Y-8A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 718. Compounds of formula I.8 wherein R¹ is Y-8B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 719. Compounds of formula I.8 wherein R¹ is Y-8B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 720. Compounds of formula I.8 wherein R¹ is Y-8B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 721. Compounds of formula I.8 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 722. Compounds of formula I.8 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 723. Compounds of formula I.8 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 724. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 725. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 726. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 727. Compounds of formula I.8 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 728. Compounds of formula I.8 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 729. Compounds of formula I.8 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 730. Compounds of formula I.8 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 731. Compounds of formula I.8 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 732. Compounds of formula I.8 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 733. Compounds of formula I.8 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 734. Compounds of formula I.8 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 735. Compounds of formula I.8 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 736. Compounds of formula I.8 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 737. Compounds of formula I.8 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 738. Compounds of formula I.8 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 739. Compounds of formula I.8 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 740. Compounds of formula I.8 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 741. Compounds of formula I.8 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 742. Compounds of formula I.8 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 743. Compounds of formula I.8 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 744. Compounds of formula I.8 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 745. Compounds of formula I.8 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 746. Compounds of formula I.8 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 747. Compounds of formula I.8 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 748. Compounds of formula I.8 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 749. Compounds of formula I.8 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 750. Compounds of formula I.8 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 751. Compounds of formula I.8 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 752. Compounds of formula I.8 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 753. Compounds of formula I.8 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 754. Compounds of formula I.8 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 755. Compounds of formula I.8 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 756. Compounds of formula I.8 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 757. Compounds of formula I.8 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 758. Compounds of formula I.8 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 759. Compounds of formula I.8 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 760. Compounds of formula I.8 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 761. Compounds of formula I.8 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 762. Compounds of formula I.8 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 763. Compounds of formula I.8 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 764. Compounds of formula I.8 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 765. Compounds of formula I.8 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 766. Compounds of formula I.8 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 767. Compounds of formula I.8 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 768. Compounds of formula I.8 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 769. Compounds of formula I.8 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 770. Compounds of formula I.8 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 771. Compounds of formula I.8 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 772. Compounds of formula I.8 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 773. Compounds of formula I.8 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 774. Compounds of formula I.8 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 775. Compounds of formula I.8 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 776. Compounds of formula I.8 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 777. Compounds of formula I.8 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 778. Compounds of formula I.8 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 779. Compounds of formula I.8 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 780. Compounds of formula I.8 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 781. Compounds of formula I.8 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 782. Compounds of formula I.8 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 783. Compounds of formula I.8 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 784. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 785. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is c-C₃H₅, R⁹ is CH₃, R¹⁰ is H.

Table 786. Compounds of formula I.8 wherein R¹ is Y-1 B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 787. Compounds of formula I.8 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 788. Compounds of formula I.8 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 789. Compounds of formula I.8 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 790. Compounds of formula I.8 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 791. Compounds of formula I.8 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 792. Compounds of formula I.8 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 793. Compounds of formula I.8 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 794. Compounds of formula I.8 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 795. Compounds of formula I.8 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 796. Compounds of formula I.8 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 797. Compounds of formula I.8 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 798. Compounds of formula I.8 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 799. Compounds of formula I.8 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 800. Compounds of formula I.8 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 801. Compounds of formula I.8 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 802. Compounds of formula I.8 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 803. Compounds of formula I.8 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 804. Compounds of formula I.8 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 805. Compounds of formula I.8 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 806. Compounds of formula I.8 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 807. Compounds of formula I.8 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 808. Compounds of formula I.8 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 809. Compounds of formula I.8 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 810. Compounds of formula I.8 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 811. Compounds of formula I.8 wherein R¹ is Y-40, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 812. Compounds of formula I.8 wherein R¹ is Y-40, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 813. Compounds of formula I.8 wherein R¹ is Y-40, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 814. Compounds of formula I.8 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 815. Compounds of formula I.8 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 816. Compounds of formula I.8 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 817. Compounds of formula I.8 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 818. Compounds of formula I.8 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 819. Compounds of formula I.8 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 820. Compounds of formula I.8 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 821. Compounds of formula I.8 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 822. Compounds of formula I.8 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 823. Compounds of formula I.8 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 824. Compounds of formula I.8 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 825. Compounds of formula I.8 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 826. Compounds of formula I.8 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 827. Compounds of formula I.8 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 828. Compounds of formula I.8 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 829. Compounds of formula I.8 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 830. Compounds of formula I.8 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 831. Compounds of formula I.8 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 832. Compounds of formula I.8 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 833. Compounds of formula I.8 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 834. Compounds of formula I.8 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 835. Compounds of formula I.8 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 836. Compounds of formula I.8 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 837. Compounds of formula I.8 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 838. Compounds of formula I.8 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 839. Compounds of formula I.8 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 840. Compounds of formula I.8 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 841. Compounds of formula I.9 wherein R¹ is Y-1A, R² is H, R⁹ is H and R¹⁰ is H.

Table 842. Compounds of formula I.9 wherein R¹ is Y-1A, R² is H, R⁹ is CH₃ and, R¹⁰ is H.

Table 843. Compounds of formula I.9 wherein R¹ is Y-1A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 844. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is H, R⁹ is H and R¹⁰ is H.

Table 845. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 846. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 847. Compounds of formula I.9 wherein R¹ is Y-2A, R² is H, R⁹ is H and R¹⁰ is H.

Table 848. Compounds of formula I.9 wherein R¹ is Y-2A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 849. Compounds of formula I.9 wherein R¹ is Y-2A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 850. Compounds of formula I.9 wherein R¹ is Y-2B, R² is H, R⁹ is H and R¹⁰ is H.

Table 851. Compounds of formula I.9 wherein R¹ is Y-2B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 852. Compounds of formula I.9 wherein R¹ is Y-2B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 853. Compounds of formula I.9 wherein R¹ is Y-3A, R² is H, R⁹ is H and R¹⁰ is H.

Table 854. Compounds of formula I.9 wherein R¹ is Y-3A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 855. Compounds of formula I.9 wherein R¹ is Y-3A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 856. Compounds of formula I.9 wherein R¹ is Y-3B, R² is H, R⁹ is H and R¹⁰ is H.

Table 857. Compounds of formula I.9 wherein R¹ is Y-3B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 858. Compounds of formula I.9 wherein R¹ is Y-3B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 859. Compounds of formula I.9 wherein R¹ is Y-3C, R² is H, R⁹ is H and R¹⁰ is H.

Table 860. Compounds of formula I.9 wherein R¹ is Y-3C, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 861. Compounds of formula I.9 wherein R¹ is Y-3C, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 862. Compounds of formula I.9 wherein R¹ is Y-3D, R² is H, R⁹ is H and R¹⁰ is H.

Table 863. Compounds of formula I.9 wherein R¹ is Y-3D, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 864. Compounds of formula I.9 wherein R¹ is Y-3D, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 865. Compounds of formula I.9 wherein R¹ is Y-4A, R² is H, R⁹ is H and R¹⁰ is H.

Table 866. Compounds of formula I.9 wherein R¹ is Y-4A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 867. Compounds of formula I.9 wherein R¹ is Y-4A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 868. Compounds of formula I.9 wherein R¹ is Y-4B, R² is H, R⁹ is H and R¹⁰ is H.

Table 869. Compounds of formula I.9 wherein R¹ is Y-4B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 870. Compounds of formula I.9 wherein R¹ is Y-4B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 871. Compounds of formula I.9 wherein R¹ is Y-4C, R² is H, R⁹ is H and R¹⁰ is H.

Table 872. Compounds of formula I.9 wherein R¹ is Y-4C, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 873. Compounds of formula I.9 wherein R¹ is Y-4C, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 874. Compounds of formula I.9 wherein R¹ is Y-4D, R² is H, R⁹ is H and R¹⁰ is H.

Table 875. Compounds of formula I.9 wherein R¹ is Y-4D, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 876. Compounds of formula I.9 wherein R¹ is Y-4D, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 877. Compounds of formula I.9 wherein R¹ is Y-5A, R² is H, R⁹ is H and R¹⁰ is H.

Table 878. Compounds of formula I.9 wherein R¹ is Y-5A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 879. Compounds of formula I.9 wherein R¹ is Y-5A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 880. Compounds of formula I.9 wherein R¹ is Y-5B, R² is H, R⁹ is H and R¹⁰ is H.

Table 881. Compounds of formula I.9 wherein R¹ is Y-5B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 882. Compounds of formula I.9 wherein R¹ is Y-5B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 883. Compounds of formula I.9 wherein R¹ is Y-6A, R² is H, R⁹ is H and R¹⁰ is H.

Table 884. Compounds of formula I.9 wherein R¹ is Y-6A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 885. Compounds of formula I.9 wherein R¹ is Y-6A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 886. Compounds of formula I.9 wherein R¹ is Y-6B, R² is H, R⁹ is H and R¹⁰ is H.

Table 887. Compounds of formula I.9 wherein R¹ is Y-6B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 888. Compounds of formula I.9 wherein R¹ is Y-6B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 889. Compounds of formula I.9 wherein R¹ is Y-7A, R² is H, R⁹ is H and R¹⁰ is H.

Table 890. Compounds of formula I.9 wherein R¹ is Y-7A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 891. Compounds of formula I.9 wherein R¹ is Y-7A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 892. Compounds of formula I.9 wherein R¹ is Y-7B, R² is H, R⁹ is H and R¹⁰ is H.

Table 893. Compounds of formula I.9 wherein R¹ is Y-7B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 894. Compounds of formula I.9 wherein R¹ is Y-7B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 895. Compounds of formula I.9 wherein R¹ is Y-8A, R² is H, R⁹ is H and R¹⁰ is H.

Table 896. Compounds of formula I.9 wherein R¹ is Y-8A, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 897. Compounds of formula I.9 wherein R¹ is Y-8A, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 898. Compounds of formula I.9 wherein R¹ is Y-8B, R² is H, R⁹ is H and R¹⁰ is H.

Table 899. Compounds of formula I.9 wherein R¹ is Y-8B, R² is H, R⁹ is CH₃ and R¹⁰ is H.

Table 900. Compounds of formula I.9 wherein R¹ is Y-8B, R² is H, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 901. Compounds of formula I.9 wherein R¹ is Y-1A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 902. Compounds of formula I.9 wherein R¹ is Y-1A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 903. Compounds of formula I.9 wherein R¹ is Y-1A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 904. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 905. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 906. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 907. Compounds of formula I.9 wherein R¹ is Y-2A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 908. Compounds of formula I.9 wherein R¹ is Y-2A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 909. Compounds of formula I.9 wherein R¹ is Y-2A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 910. Compounds of formula I.9 wherein R¹ is Y-2B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 911. Compounds of formula I.9 wherein R¹ is Y-2B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 912. Compounds of formula I.9 wherein R¹ is Y-2B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 913. Compounds of formula I.9 wherein R¹ is Y-3A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 914. Compounds of formula I.9 wherein R¹ is Y-3A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 915. Compounds of formula I.9 wherein R¹ is Y-3A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 916. Compounds of formula I.9 wherein R¹ is Y-3B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 917. Compounds of formula I.9 wherein R¹ is Y-3B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 918. Compounds of formula I.9 wherein R¹ is Y-3B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 919. Compounds of formula I.9 wherein R¹ is Y-3C, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 920. Compounds of formula I.9 wherein R¹ is Y-3C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 921. Compounds of formula I.9 wherein R¹ is Y-3C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 922. Compounds of formula I.9 wherein R¹ is Y-3D, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 923. Compounds of formula I.9 wherein R¹ is Y-3D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 924. Compounds of formula I.9 wherein R¹ is Y-3D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 925. Compounds of formula I.9 wherein R¹ is Y-4A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 926. Compounds of formula I.9 wherein R¹ is Y-4A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 927. Compounds of formula I.9 wherein R¹ is Y-4A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 928. Compounds of formula I.9 wherein R¹ is Y-4B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 929. Compounds of formula I.9 wherein R¹ is Y-4B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 930. Compounds of formula I.9 wherein R¹ is Y-4B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 931. Compounds of formula I.9 wherein R¹ is Y-4C, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 932. Compounds of formula I.9 wherein R¹ is Y-4C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 933. Compounds of formula I.9 wherein R¹ is Y-4C, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 934. Compounds of formula I.9 wherein R¹ is Y-4D, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 935. Compounds of formula I.9 wherein R¹ is Y-4D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 936. Compounds of formula I.9 wherein R¹ is Y-4D, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 937. Compounds of formula I.9 wherein R¹ is Y-5A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 938. Compounds of formula I.9 wherein R¹ is Y-5A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 939. Compounds of formula I.9 wherein R¹ is Y-5A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 940. Compounds of formula I.9 wherein R¹ is Y-5B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 941. Compounds of formula I.9 wherein R¹ is Y-5B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 942. Compounds of formula I.9 wherein R¹ is Y-5B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 943. Compounds of formula I.9 wherein R¹ is Y-6A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 944. Compounds of formula I.9 wherein R¹ is Y-6A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 945. Compounds of formula I.9 wherein R¹ is Y-6A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 946. Compounds of formula I.9 wherein R¹ is Y-6B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 947. Compounds of formula I.9 wherein R¹ is Y-6B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 948. Compounds of formula I.9 wherein R¹ is Y-6B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 949. Compounds of formula I.9 wherein R¹ is Y-7A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 950. Compounds of formula I.9 wherein R¹ is Y-7A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 951. Compounds of formula I.9 wherein R¹ is Y-7A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 952. Compounds of formula I.9 wherein R¹ is Y-7B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 953. Compounds of formula I.9 wherein R¹ is Y-7B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 954. Compounds of formula I.9 wherein R¹ is Y-7B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 955. Compounds of formula I.9 wherein R¹ is Y-8A, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 956. Compounds of formula I.9 wherein R¹ is Y-8A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 957. Compounds of formula I.9 wherein R¹ is Y-8A, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 958. Compounds of formula I.9 wherein R¹ is Y-8B, R² is CH₃, R⁹ is H and R¹⁰ is H.

Table 959. Compounds of formula I.9 wherein R¹ is Y-8B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is H.

Table 960. Compounds of formula I.9 wherein R¹ is Y-8B, R² is CH₃, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 961. Compounds of formula I.9 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 962. Compounds of formula I.9 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 963. Compounds of formula I.9 wherein R¹ is Y-1A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 964. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 965. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 966. Compounds of formula I.9 wherein R¹ is Y-1 B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 967. Compounds of formula I.9 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 968. Compounds of formula I.9 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 969. Compounds of formula I.9 wherein R¹ is Y-2A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 970. Compounds of formula I.9 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 971. Compounds of formula I.9 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 972. Compounds of formula I.9 wherein R¹ is Y-2B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 973. Compounds of formula I.9 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 974. Compounds of formula I.9 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 975. Compounds of formula I.9 wherein R¹ is Y-3A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 976. Compounds of formula I.9 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 977. Compounds of formula I.9 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 978. Compounds of formula I.9 wherein R¹ is Y-3B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 979. Compounds of formula I.9 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 980. Compounds of formula I.9 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 981. Compounds of formula I.9 wherein R¹ is Y-3C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 982. Compounds of formula I.9 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 983. Compounds of formula I.9 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 984. Compounds of formula I.9 wherein R¹ is Y-3D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 985. Compounds of formula I.9 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 986. Compounds of formula I.9 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 987. Compounds of formula I.9 wherein R¹ is Y-4A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 988. Compounds of formula I.9 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 989. Compounds of formula I.9 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 990. Compounds of formula I.9 wherein R¹ is Y-4B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 991. Compounds of formula I.9 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 992. Compounds of formula I.9 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 993. Compounds of formula I.9 wherein R¹ is Y-4C, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 994. Compounds of formula I.9 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 995. Compounds of formula I.9 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 996. Compounds of formula I.9 wherein R¹ is Y-4D, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 997. Compounds of formula I.9 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 998. Compounds of formula I.9 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 999. Compounds of formula I.9 wherein R¹ is Y-5A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1000. Compounds of formula I.9 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 1001. Compounds of formula I.9 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1002. Compounds of formula I.9 wherein R¹ is Y-5B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1003. Compounds of formula I.9 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 1004. Compounds of formula I.9 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1005. Compounds of formula I.9 wherein R¹ is Y-6A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1006. Compounds of formula I.9 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 1007. Compounds of formula I.9 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1008. Compounds of formula I.9 wherein R¹ is Y-6B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1009. Compounds of formula I.9 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 1010. Compounds of formula I.9 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1011. Compounds of formula I.9 wherein R¹ is Y-7A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1012. Compounds of formula I.9 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 1013. Compounds of formula I.9 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1014. Compounds of formula I.9 wherein R¹ is Y-7B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1015. Compounds of formula I.9 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 1016. Compounds of formula I.9 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1017. Compounds of formula I.9 wherein R¹ is Y-8A, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1018. Compounds of formula I.9 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is H and R¹⁰ is H.

Table 1019. Compounds of formula I.9 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1020. Compounds of formula I.9 wherein R¹ is Y-8B, R² is C₂H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1021. Compounds of formula I.9 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1022. Compounds of formula I.9 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1023. Compounds of formula I.9 wherein R¹ is Y-1A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1024. Compounds of formula I.9 wherein R¹ is Y-1B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1025. Compounds of formula I.9 wherein R¹ is Y-1B, R² is c-C₃H₅, R⁹ is CH₃, R¹⁰ is H.

Table 1026. Compounds of formula I.9 wherein R¹ is Y-1B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1027. Compounds of formula I.9 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1028. Compounds of formula I.9 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1029. Compounds of formula I.9 wherein R¹ is Y-2A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1030. Compounds of formula I.9 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1031. Compounds of formula I.9 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1032. Compounds of formula I.9 wherein R¹ is Y-2B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1033. Compounds of formula I.9 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1034. Compounds of formula I.9 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1035. Compounds of formula I.9 wherein R¹ is Y-3A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1036. Compounds of formula I.9 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1037. Compounds of formula I.9 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1038. Compounds of formula I.9 wherein R¹ is Y-3B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1039. Compounds of formula I.9 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1040. Compounds of formula I.9 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1041. Compounds of formula I.9 wherein R¹ is Y-3C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1042. Compounds of formula I.9 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1043. Compounds of formula I.9 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1044. Compounds of formula I.9 wherein R¹ is Y-3D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1045. Compounds of formula I.9 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1046. Compounds of formula I.9 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1047. Compounds of formula I.9 wherein R¹ is Y-4A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1048. Compounds of formula I.9 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1049. Compounds of formula I.9 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1050. Compounds of formula I.9 wherein R¹ is Y-4B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1051. Compounds of formula I.9 wherein R¹ is Y-4C, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1052. Compounds of formula I.9 wherein R¹ is Y-4C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1053. Compounds of formula I.9 wherein R¹ is Y-4C, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1054. Compounds of formula I.9 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1055. Compounds of formula I.9 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1056. Compounds of formula I.9 wherein R¹ is Y-4D, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1057. Compounds of formula I.9 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1058. Compounds of formula I.9 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1059. Compounds of formula I.9 wherein R¹ is Y-5A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1060. Compounds of formula I.9 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1061. Compounds of formula I.9 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1062. Compounds of formula I.9 wherein R¹ is Y-5B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1063. Compounds of formula I.9 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1064. Compounds of formula I.9 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1065. Compounds of formula I.9 wherein R¹ is Y-6A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1066. Compounds of formula I.9 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1067. Compounds of formula I.9 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1068. Compounds of formula I.9 wherein R¹ is Y-6B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1069. Compounds of formula I.9 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1070. Compounds of formula I.9 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1071. Compounds of formula I.9 wherein R¹ is Y-7A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1072. Compounds of formula I.9 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1073. Compounds of formula I.9 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1074. Compounds of formula I.9 wherein R¹ is Y-7B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1075. Compounds of formula I.9 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1076. Compounds of formula I.9 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1077. Compounds of formula I.9 wherein R¹ is Y-8A, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1078. Compounds of formula I.9 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is H and R¹⁰ is H.

Table 1079. Compounds of formula I.9 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is H.

Table 1080. Compounds of formula I.9 wherein R¹ is Y-8B, R² is c-C₃H₅, R⁹ is CH₃ and R¹⁰ is CH₃.

Table 1081. Compounds of formula I.13 wherein R¹ is Y-1A and R² is H.

Table 1082. Compounds of formula I.13 wherein R¹ is Y-1B and R² is H.

Table 1083. Compounds of formula I.13 wherein R¹ is Y-2A and R² is H.

Table 1084. Compounds of formula I.13 wherein R¹ is Y-2B and R² is H.

Table 1085. Compounds of formula I.13 wherein R¹ is Y-3A and R² is H.

Table 1086. Compounds of formula I.13 wherein R¹ is Y-3B and R² is H.

Table 1087. Compounds of formula I.13 wherein R¹ is Y-3C and R² is H.

Table 1088. Compounds of formula I.13 wherein R¹ is Y-3D and R² is H.

Table 1089. Compounds of formula I.13 wherein R¹ is Y-4A and R² is H.

Table 1090. Compounds of formula I.13 wherein R¹ is Y-4B and R² is H.

Table 1091. Compounds of formula I.13 wherein R¹ is Y-4C and R² is H.

Table 1092. Compounds of formula I.13 wherein R¹ is Y-4D and R² is H.

Table 1093. Compounds of formula I.13 wherein R¹ is Y-5A and R² is H.

Table 1094. Compounds of formula I.13 wherein R¹ is Y-5B and R² is H.

Table 1095. Compounds of formula I.13 wherein R¹ is Y-6A and R² is H.

Table 1096. Compounds of formula I.13 wherein R¹ is Y-6B and R² is H.

Table 1097. Compounds of formula I.13 wherein R¹ is Y-7A and R² is H.

Table 1098. Compounds of formula I.13 wherein R¹ is Y-7B and R² is H.

Table 1099. Compounds of formula I.13 wherein R¹ is Y-8A and R² is H.

Table 1100. Compounds of formula I.13 wherein R¹ is Y-8B and R² is H.

Table 1101. Compounds of formula I.13 wherein R¹ is Y-1A and R² is CH₃.

Table 1102. Compounds of formula I.13 wherein R¹ is Y-1B and R² is CH₃.

Table 1103. Compounds of formula I.13 wherein R¹ is Y-2A and R² is CH₃.

Table 1104. Compounds of formula I.13 wherein R¹ is Y-2B and R² is CH₃.

Table 1105. Compounds of formula I.13 wherein R¹ is Y-3A and R² is CH₃.

Table 1106. Compounds of formula I.13 wherein R¹ is Y-3B and R² is CH₃.

Table 1107. Compounds of formula I.13 wherein R¹ is Y-3C and R² is CH₃.

Table 1108. Compounds of formula I.13 wherein R¹ is Y-3D and R² is CH₃.

Table 1109. Compounds of formula I.13 wherein R¹ is Y-4A and R² is CH₃.

Table 1110. Compounds of formula I.13 wherein R¹ is Y-4B and R² is CH₃.

Table 1111. Compounds of formula I.13 wherein R¹ is Y-4C and R² is CH₃.

Table 1112. Compounds of formula I.13 wherein R¹ is Y-4D and R² is CH₃.

Table 1113. Compounds of formula I.13 wherein R¹ is Y-5A and R² is CH₃.

Table 1114. Compounds of formula I.13 wherein R¹ is Y-5B and R² is CH₃.

Table 1115. Compounds of formula I.13 wherein R¹ is Y-6A and R² is CH₃.

Table 1116. Compounds of formula I.13 wherein R¹ is Y-6B and R² is CH₃.

Table 1117. Compounds of formula I.13 wherein R¹ is Y-7A and R² is CH₃.

Table 1118. Compounds of formula I.13 wherein R¹ is Y-7B and R² is CH₃.

Table 1119. Compounds of formula I.13 wherein R¹ is Y-8A and R² is CH₃.

Table 1120. Compounds of formula I.13 wherein R¹ is Y-8B and R² is CH₃.

Table 1121. Compounds of formula I.13 wherein R¹ is Y-1A and R² is c-C₃H₅.

Table 1122. Compounds of formula I.13 wherein R¹ is Y-1B and R² is c-C₃H₅.

Table 1123. Compounds of formula I.13 wherein R¹ is Y-2A and R² is c-C₃H₅.

Table 1124. Compounds of formula I.13 wherein R¹ is Y-2B and R² is c-C₃H₅.

Table 1125. Compounds of formula I.13 wherein R¹ is Y-3A and R² is c-C₃H₅.

Table 1126. Compounds of formula I.13 wherein R¹ is Y-3B and R² is c-C₃H₅.

Table 1127. Compounds of formula I.13 wherein R¹ is Y-3C and R² is c-C₃H₅.

Table 1128. Compounds of formula I.13 wherein R¹ is Y-3D and R² is c-C₃H₅.

Table 1129. Compounds of formula I.13 wherein R¹ is Y-4A and R² is c-C₃H₅.

Table 1130. Compounds of formula I.13 wherein R¹ is Y-4B and R² is c-C₃H₅.

Table 1131. Compounds of formula I.13 wherein R¹ is Y-4C and R² is c-C₃H₅.

Table 1132. Compounds of formula I.13 wherein R¹ is Y-4D and R² is c-C₃H₅.

Table 1133. Compounds of formula I.13 wherein R¹ is Y-5A and R² is c-C₃H₅.

Table 1134. Compounds of formula I.13 wherein R¹ is Y-5B and R² is c-C₃H₅.

Table 1135. Compounds of formula I.13 wherein R¹ is Y-6A and R² is c-C₃H₅.

Table 1136. Compounds of formula I.13 wherein R¹ is Y-6B and R² is c-C₃H₅.

Table 1137. Compounds of formula I.13 wherein R¹ is Y-7A and R² is c-C₃H₅.

Table 1138. Compounds of formula I.13 wherein R¹ is Y-7B and R² is c-C₃H₅.

Table 1139. Compounds of formula I.13 wherein R¹ is Y-8A and R² is c-C₃H₅.

Table 1140. Compounds of formula I.13 wherein R¹ is Y-8B and R² is c-C₃H₅.

Table 1141. Compounds of formula I.14 wherein R¹ is Y-1A and R² is H.

Table 1142. Compounds of formula I.14 wherein R¹ is Y-1B and R² is H.

Table 1143. Compounds of formula I.14 wherein R¹ is Y-2A and R² is H.

Table 1144. Compounds of formula I.14 wherein R¹ is Y-2B and R² is H.

Table 1145. Compounds of formula I.14 wherein R¹ is Y-3A and R² is H.

Table 1146. Compounds of formula I.14 wherein R¹ is Y-3B and R² is H.

Table 1147. Compounds of formula I.14 wherein R¹ is Y-3C and R² is H.

Table 1148. Compounds of formula I.14 wherein R¹ is Y-3D and R² is H.

Table 1149. Compounds of formula I.14 wherein R¹ is Y-4A and R² is H.

Table 1150. Compounds of formula I.14 wherein R¹ is Y-4B and R² is H.

Table 1151. Compounds of formula I.14 wherein R¹ is Y-4C and R² is H.

Table 1152. Compounds of formula I.14 wherein R¹ is Y-4D and R² is H.

Table 1153. Compounds of formula I.14 wherein R¹ is Y-5A and R² is H.

Table 1154. Compounds of formula I.14 wherein R¹ is Y-5B and R² is H.

Table 1155. Compounds of formula I.14 wherein R¹ is Y-6A and R² is H.

Table 1156. Compounds of formula I.14 wherein R¹ is Y-6B and R² is H.

Table 1157. Compounds of formula I.14 wherein R¹ is Y-7A and R² is H.

Table 1158. Compounds of formula I.14 wherein R¹ is Y-7B and R² is H.

Table 1159. Compounds of formula I.14 wherein R¹ is Y-8A and R² is H.

Table 1160. Compounds of formula I.14 wherein R¹ is Y-8B and R² is H.

Table 1161. Compounds of formula I.14 wherein R¹ is Y-1A and R² is CH₃.

Table 1162. Compounds of formula I.14 wherein R¹ is Y-1B and R² is CH₃.

Table 1163. Compounds of formula I.14 wherein R¹ is Y-2A and R² is CH₃.

Table 1164. Compounds of formula I.14 wherein R¹ is Y-2B and R² is CH₃.

Table 1165. Compounds of formula I.14 wherein R¹ is Y-3A and R² is CH₃.

Table 1166. Compounds of formula I.14 wherein R¹ is Y-3B and R² is CH₃.

Table 1167. Compounds of formula I.14 wherein R¹ is Y-3C and R² is CH₃.

Table 1168. Compounds of formula I.14 wherein R¹ is Y-3D and R² is CH₃.

Table 1169. Compounds of formula I.14 wherein R¹ is Y-4A and R² is CH₃.

Table 1170. Compounds of formula I.14 wherein R¹ is Y-4B and R² is CH₃.

Table 1171. Compounds of formula I.14 wherein R¹ is Y-4C and R² is CH₃.

Table 1172. Compounds of formula I.14 wherein R¹ is Y-4D and R² is CH₃.

Table 1173. Compounds of formula I.14 wherein R¹ is Y-5A and R² is CH₃.

Table 1174. Compounds of formula I.14 wherein R¹ is Y-5B and R² is CH₃.

Table 1175. Compounds of formula I.14 wherein R¹ is Y-6A and R² is CH₃.

Table 1176. Compounds of formula I.14 wherein R¹ is Y-6B and R² is CH₃.

Table 1177. Compounds of formula I.14 wherein R¹ is Y-7A and R² is CH₃.

Table 1178. Compounds of formula I.14 wherein R¹ is Y-7B and R² is CH₃.

Table 1179. Compounds of formula I.14 wherein R¹ is Y-8A and R² is CH₃.

Table 1180. Compounds of formula I.14 wherein R¹ is Y-8B and R² is CH₃.

Table 1181. Compounds of formula I.14 wherein R¹ is Y-1A and R² is c-C₃H₅.

Table 1182. Compounds of formula I.14 wherein R¹ is Y-1B and R² is c-C₃H₅.

Table 1183. Compounds of formula I.14 wherein R¹ is Y-2A and R² is c-C₃H₅.

Table 1184. Compounds of formula I.14 wherein R¹ is Y-2B and R² is c-C₃H₅.

Table 1185. Compounds of formula I.14 wherein R¹ is Y-3A and R² is c-C₃H₅.

Table 1186. Compounds of formula I.14 wherein R¹ is Y-3B and R² is c-C₃H₅.

Table 1187. Compounds of formula I.14 wherein R¹ is Y-3C and R² is c-C₃H₅.

Table 1188. Compounds of formula I.14 wherein R¹ is Y-3D and R² is c-C₃H₅.

Table 1189. Compounds of formula I.14 wherein R¹ is Y-4A and R² is c-C₃H₅.

Table 1190. Compounds of formula I.14 wherein R¹ is Y-4B and R² is c-C₃H₅.

Table 1191. Compounds of formula I.14 wherein R¹ is Y-4C and R² is c-C₃H₅.

Table 1192. Compounds of formula I.14 wherein R¹ is Y-4D and R² is c-C₃H₅.

Table 1193. Compounds of formula I.14 wherein R¹ is Y-5A and R² is c-C₃H₅.

Table 1194. Compounds of formula I.14 wherein R¹ is Y-5B and R² is c-C₃H₅.

Table 1195. Compounds of formula I.14 wherein R¹ is Y-6A and R² is c-C₃H₅.

Table 1196. Compounds of formula I.14 wherein R¹ is Y-6B and R² is c-C₃H₅.

Table 1197. Compounds of formula I.14 wherein R¹ is Y-7A and R² is c-C₃H₅.

Table 1198. Compounds of formula I.14 wherein R¹ is Y-7B and R² is c-C₃H₅.

Table 1199. Compounds of formula I.14 wherein R¹ is Y-8A and R² is c-C₃H₅.

Table 1200. Compounds of formula I.14 wherein R¹ is Y-8B and R² is c-C₃H₅.

Table 1201. Compounds of formula I.15 wherein R¹ is Y-1A and R² is H.

Table 1202. Compounds of formula I.15 wherein R¹ is Y-1B and R² is H.

Table 1203. Compounds of formula I.15 wherein R¹ is Y-2A and R² is H.

Table 1204. Compounds of formula I.15 wherein R¹ is Y-2B and R² is H.

Table 1205. Compounds of formula I.15 wherein R¹ is Y-3A and R² is H.

Table 1206. Compounds of formula I.15 wherein R¹ is Y-3B and R² is H.

Table 1207. Compounds of formula I.15 wherein R¹ is Y-3C and R² is H.

Table 1208. Compounds of formula I.15 wherein R¹ is Y-3D and R² is H.

Table 1209. Compounds of formula I.15 wherein R¹ is Y-4A and R² is H.

Table 1210. Compounds of formula I.15 wherein R¹ is Y-4B and R² is H.

Table 1211. Compounds of formula I.15 wherein R¹ is Y-4C and R² is H.

Table 1212. Compounds of formula I.15 wherein R¹ is Y-4D and R² is H.

Table 1213. Compounds of formula I.15 wherein R¹ is Y-5A and R² is H.

Table 1214. Compounds of formula I.15 wherein R¹ is Y-5B and R² is H.

Table 1215. Compounds of formula I.15 wherein R¹ is Y-6A and R² is H.

Table 1216. Compounds of formula I.15 wherein R¹ is Y-6B and R² is H.

Table 1217. Compounds of formula I.15 wherein R¹ is Y-7A and R² is H.

Table 1218. Compounds of formula I.15 wherein R¹ is Y-7B and R² is H.

Table 1219. Compounds of formula I.15 wherein R¹ is Y-8A and R² is H.

Table 1220. Compounds of formula I.15 wherein R¹ is Y-8B and R² is H.

Table 1221. Compounds of formula I.15 wherein R¹ is Y-1A and R² is CH₃.

Table 1222. Compounds of formula I.15 wherein R¹ is Y-1B and R² is CH₃.

Table 1223. Compounds of formula I.15 wherein R¹ is Y-2A and R² is CH₃.

Table 1224. Compounds of formula I.15 wherein R¹ is Y-2B and R² is CH₃.

Table 1225. Compounds of formula I.15 wherein R¹ is Y-3A and R² is CH₃.

Table 1226. Compounds of formula I.15 wherein R¹ is Y-3B and R² is CH₃.

Table 1227. Compounds of formula I.15 wherein R¹ is Y-3C and R² is CH₃.

Table 1228. Compounds of formula I.15 wherein R¹ is Y-3D and R² is CH₃.

Table 1229. Compounds of formula I.15 wherein R¹ is Y-4A and R² is CH₃.

Table 1230. Compounds of formula I.15 wherein R¹ is Y-4B and R² is CH₃.

Table 1231. Compounds of formula I.15 wherein R¹ is Y-4C and R² is CH₃.

Table 1232. Compounds of formula I.15 wherein R¹ is Y-4D and R² is CH₃.

Table 1233. Compounds of formula I.15 wherein R¹ is Y-5A and R² is CH₃.

Table 1234. Compounds of formula I.15 wherein R¹ is Y-5B and R² is CH₃.

Table 1235. Compounds of formula I.15 wherein R¹ is Y-6A and R² is CH₃.

Table 1236. Compounds of formula I.15 wherein R¹ is Y-6B and R² is CH₃.

Table 1237. Compounds of formula I.15 wherein R¹ is Y-7A and R² is CH₃.

Table 1238. Compounds of formula I.15 wherein R¹ is Y-7B and R² is CH₃.

Table 1239. Compounds of formula I.15 wherein R¹ is Y-8A and R² is CH₃.

Table 1240. Compounds of formula I.15 wherein R¹ is Y-8B and R² is CH₃.

Table 1241. Compounds of formula I.15 wherein R¹ is Y-1A and R² is c-C₃H₅.

Table 1242. Compounds of formula I.15 wherein R¹ is Y-1B and R² is c-C₃H₅.

Table 1243. Compounds of formula I.15 wherein R¹ is Y-2A and R² is c-C₃H₅.

Table 1244. Compounds of formula I.15 wherein R¹ is Y-2B and R² is c-C₃H₅.

Table 1245. Compounds of formula I.15 wherein R¹ is Y-3A and R² is c-C₃H₅.

Table 1246. Compounds of formula I.15 wherein R¹ is Y-3B and R² is c-C₃H₅.

Table 1247. Compounds of formula I.15 wherein R¹ is Y-3C and R² is c-C₃H₅.

Table 1248. Compounds of formula I.15 wherein R¹ is Y-3D and R² is c-C₃H₅.

Table 1249. Compounds of formula I.15 wherein R¹ is Y-4A and R² is c-C₃H₅.

Table 1250. Compounds of formula I.15 wherein R¹ is Y-4B and R² is c-C₃H₅.

Table 1251. Compounds of formula I.15 wherein R¹ is Y-4C and R² is c-C₃H₅.

Table 1252. Compounds of formula I.15 wherein R¹ is Y-4D and R² is c-C₃H₅.

Table 1253. Compounds of formula I.15 wherein R¹ is Y-5A and R² is c-C₃H₅.

Table 1254. Compounds of formula I.15 wherein R¹ is Y-5B and R² is c-C₃H₅.

Table 1255. Compounds of formula I.15 wherein R¹ is Y-6A and R² is c-C₃H₅.

Table 1256. Compounds of formula I.15 wherein R¹ is Y-6B and R² is c-C₃H₅.

Table 1257. Compounds of formula I.15 wherein R¹ is Y-7A and R² is c-C₃H₅.

Table 1258. Compounds of formula I.15 wherein R¹ is Y-7B and R² is c-C₃H₅.

Table 1259. Compounds of formula I.15 wherein R¹ is Y-8A and R² is c-C₃H₅.

Table 1260. Compounds of formula I.15 wherein R¹ is Y-8B and R² is c-C₃H₅.

Table 1261. Compounds of formula I.16 wherein R¹ is Y-1A and R² is H.

Table 1262. Compounds of formula I.16 wherein R¹ is Y-1B and R² is H.

Table 1263. Compounds of formula I.16 wherein R¹ is Y-2A and R² is H.

Table 1264. Compounds of formula I.16 wherein R¹ is Y-2B and R² is H.

Table 1265. Compounds of formula I.16 wherein R¹ is Y-3A and R² is H.

Table 1266. Compounds of formula I.16 wherein R¹ is Y-3B and R² is H.

Table 1267. Compounds of formula I.16 wherein R¹ is Y-3C and R² is H.

Table 1268. Compounds of formula I.16 wherein R¹ is Y-3D and R² is H.

Table 1269. Compounds of formula I.16 wherein R¹ is Y-4A and R² is H.

Table 1270. Compounds of formula I.16 wherein R¹ is Y-4B and R² is H.

Table 1271. Compounds of formula I.16 wherein R¹ is Y-4C and R² is H.

Table 1272. Compounds of formula I.16 wherein R¹ is Y-4D and R² is H.

Table 1273. Compounds of formula I.16 wherein R¹ is Y-5A and R² is H.

Table 1274. Compounds of formula I.16 wherein R¹ is Y-5B and R² is H.

Table 1275. Compounds of formula I.16 wherein R¹ is Y-6A and R² is H.

Table 1276. Compounds of formula I.16 wherein R¹ is Y-6B and R² is H.

Table 1277. Compounds of formula I.16 wherein R¹ is Y-7A and R² is H.

Table 1278. Compounds of formula I.16 wherein R¹ is Y-7B and R² is H.

Table 1279. Compounds of formula I.16 wherein R¹ is Y-8A and R² is H.

Table 1280. Compounds of formula I.16 wherein R¹ is Y-8B and R² is H.

Table 1281. Compounds of formula I.16 wherein R¹ is Y-1A and R² is CH₃.

Table 1282. Compounds of formula I.16 wherein R¹ is Y-1B and R² is CH₃.

Table 1283. Compounds of formula I.16 wherein R¹ is Y-2A and R² is CH₃.

Table 1284. Compounds of formula I.16 wherein R¹ is Y-2B and R² is CH₃.

Table 1285. Compounds of formula I.16 wherein R¹ is Y-3A and R² is CH₃.

Table 1286. Compounds of formula I.16 wherein R¹ is Y-3B and R² is CH₃.

Table 1287. Compounds of formula I.16 wherein R¹ is Y-3C and R² is CH₃.

Table 1288. Compounds of formula I.16 wherein R¹ is Y-3D and R² is CH₃.

Table 1289. Compounds of formula I.16 wherein R¹ is Y-4A and R² is CH₃.

Table 1290. Compounds of formula I.16 wherein R¹ is Y-4B and R² is CH₃.

Table 1291. Compounds of formula I.16 wherein R¹ is Y-4C and R² is CH₃.

Table 1292. Compounds of formula I.16 wherein R¹ is Y-4D and R² is CH₃.

Table 1293. Compounds of formula I.16 wherein R¹ is Y-5A and R² is CH₃.

Table 1294. Compounds of formula I.16 wherein R¹ is Y-5B and R² is CH₃.

Table 1295. Compounds of formula I.16 wherein R¹ is Y-6A and R² is CH₃.

Table 1296. Compounds of formula I.16 wherein R¹ is Y-6B and R² is CH₃.

Table 1297. Compounds of formula I.16 wherein R¹ is Y-7A and R² is CH₃.

Table 1298. Compounds of formula I.16 wherein R¹ is Y-7B and R² is CH₃.

Table 1299. Compounds of formula I.16 wherein R¹ is Y-8A and R² is CH₃.

Table 1300. Compounds of formula I.16 wherein R¹ is Y-8B and R² is CH₃.

Table 1301. Compounds of formula I.16 wherein R¹ is Y-1A and R² is c-C₃H₅.

Table 1302. Compounds of formula I.16 wherein R¹ is Y-1B and R² is c-C₃H₅.

Table 1303. Compounds of formula I.16 wherein R¹ is Y-2A and R² is c-C₃H₅.

Table 1304. Compounds of formula I.16 wherein R¹ is Y-2B and R² is c-C₃H₅.

Table 1305. Compounds of formula I.16 wherein R¹ is Y-3A and R² is c-C₃H₅.

Table 1306. Compounds of formula I.16 wherein R¹ is Y-3B and R² is c-C₃H₅.

Table 1307. Compounds of formula I.16 wherein R¹ is Y-3C and R² is c-C₃H₅.

Table 1308. Compounds of formula I.16 wherein R¹ is Y-3D and R² is c-C₃H₅.

Table 1309. Compounds of formula I.16 wherein R¹ is Y-4A and R² is c-C₃H₅.

Table 1310. Compounds of formula I.16 wherein R¹ is Y-4B and R² is c-C₃H₅.

Table 1311. Compounds of formula I.16 wherein R¹ is Y-4C and R² is c-C₃H₅.

Table 1312. Compounds of formula I.16 wherein R¹ is Y-4D and R² is c-C₃H₅.

Table 1313. Compounds of formula I.16 wherein R¹ is Y-5A and R² is c-C₃H₅.

Table 1314. Compounds of formula I.16 wherein R¹ is Y-5B and R² is c-C₃H₅.

Table 1315. Compounds of formula I.16 wherein R¹ is Y-6A and R² is c-C₃H₅.

Table 1316. Compounds of formula I.16 wherein R¹ is Y-6B and R² is c-C₃H₅.

Table 1317. Compounds of formula I.16 wherein R¹ is Y-7A and R² is c-C₃H₅.

Table 1318. Compounds of formula I.16 wherein R¹ is Y-7B and R² is c-C₃H₅.

Table 1319. Compounds of formula I.16 wherein R¹ is Y-8A and R² is c-C₃H₅.

Table 1320. Compounds of formula I.16 wherein R¹ is Y-8B and R² is c-C₃H₅.

Table 1321. Compounds of formula I.17 wherein R¹ is Y-1A and R² is H.

Table 1322. Compounds of formula I.17 wherein R¹ is Y-1B and R² is H.

Table 1323. Compounds of formula I.17 wherein R¹ is Y-2A and R² is H.

Table 1324. Compounds of formula I.17 wherein R¹ is Y-2B and R² is H.

Table 1325. Compounds of formula I.17 wherein R¹ is Y-3A and R² is H.

Table 1326. Compounds of formula I.17 wherein R¹ is Y-3B and R² is H.

Table 1327. Compounds of formula I.17 wherein R¹ is Y-3C and R² is H.

Table 1328. Compounds of formula I.17 wherein R¹ is Y-3D and R² is H.

Table 1329. Compounds of formula I.17 wherein R¹ is Y-4A and R² is H.

Table 1330. Compounds of formula I.17 wherein R¹ is Y-4B and R² is H.

Table 1331. Compounds of formula I.17 wherein R¹ is Y-4C and R² is H.

Table 1332. Compounds of formula I.17 wherein R¹ is Y-4D and R² is H.

Table 1333. Compounds of formula I.17 wherein R¹ is Y-5A and R² is H.

Table 1334. Compounds of formula I.17 wherein R¹ is Y-5B and R² is H.

Table 1335. Compounds of formula I.17 wherein R¹ is Y-6A and R² is H.

Table 1336. Compounds of formula I.17 wherein R¹ is Y-6B and R² is H.

Table 1337. Compounds of formula I.17 wherein R¹ is Y-7A and R² is H.

Table 1338. Compounds of formula I.17 wherein R¹ is Y-7B and R² is H.

Table 1339. Compounds of formula I.17 wherein R¹ is Y-8A and R² is H.

Table 1340. Compounds of formula I.17 wherein R¹ is Y-8B and R² is H.

Table 1341. Compounds of formula I.17 wherein R¹ is Y-1A and R² is CH₃.

Table 1342. Compounds of formula I.17 wherein R¹ is Y-1B and R² is CH₃.

Table 1343. Compounds of formula I.17 wherein R¹ is Y-2A and R² is CH₃.

Table 1344. Compounds of formula I.17 wherein R¹ is Y-2B and R² is CH₃.

Table 1345. Compounds of formula I.17 wherein R¹ is Y-3A and R² is CH₃.

Table 1346. Compounds of formula I.17 wherein R¹ is Y-3B and R² is CH₃.

Table 1347. Compounds of formula I.17 wherein R¹ is Y-3C and R² is CH₃.

Table 1348. Compounds of formula I.17 wherein R¹ is Y-3D and R² is CH₃.

Table 1349. Compounds of formula I.17 wherein R¹ is Y-4A and R² is CH₃.

Table 1350. Compounds of formula I.17 wherein R¹ is Y-4B and R² is CH₃.

Table 1351. Compounds of formula I.17 wherein R¹ is Y-4C and R² is CH₃.

Table 1352. Compounds of formula I.17 wherein R¹ is Y-4D and R² is CH₃.

Table 1353. Compounds of formula I.17 wherein R¹ is Y-5A and R² is CH₃.

Table 1354. Compounds of formula I.17 wherein R¹ is Y-5B and R² is CH₃.

Table 1355. Compounds of formula I.17 wherein R¹ is Y-6A and R² is CH₃.

Table 1356. Compounds of formula I.17 wherein R¹ is Y-6B and R² is CH₃.

Table 1357. Compounds of formula I.17 wherein R¹ is Y-7A and R² is CH₃.

Table 1358. Compounds of formula I.17 wherein R¹ is Y-7B and R² is CH₃.

Table 1359. Compounds of formula I.17 wherein R¹ is Y-8A and R² is CH₃.

Table 1360. Compounds of formula I.17 wherein R¹ is Y-8B and R² is CH₃.

Table 1361. Compounds of formula I.17 wherein R¹ is Y-1A and R² is c-C₃H₅.

Table 1362. Compounds of formula I.17 wherein R¹ is Y-1B and R² is c-C₃H₅.

Table 1363. Compounds of formula I.17 wherein R¹ is Y-2A and R² is c-C₃H₅.

Table 1364. Compounds of formula I.17 wherein R¹ is Y-2B and R² is c-C₃H₅.

Table 1365. Compounds of formula I.17 wherein R¹ is Y-3A and R² is c-C₃H₅.

Table 1366. Compounds of formula I.17 wherein R¹ is Y-3B and R² is c-C₃H₅.

Table 1367. Compounds of formula I.17 wherein R¹ is Y-3C and R² is c-C₃H₅.

Table 1368. Compounds of formula I.17 wherein R¹ is Y-3D and R² is c-C₃H₅.

Table 1369. Compounds of formula I.17 wherein R¹ is Y-4A and R² is c-C₃H₅.

Table 1370. Compounds of formula I.17 wherein R¹ is Y-4B and R² is c-C₃H₅.

Table 1371. Compounds of formula I.17 wherein R¹ is Y-4C and R² is c-C₃H₅.

Table 1372. Compounds of formula I.17 wherein R¹ is Y-4D and R² is c-C₃H₅.

Table 1373. Compounds of formula I.17 wherein R¹ is Y-5A and R² is c-C₃H₅.

Table 1374. Compounds of formula I.17 wherein R¹ is Y-5B and R² is c-C₃H₅.

Table 1375. Compounds of formula I.17 wherein R¹ is Y-6A and R² is c-C₃H₅.

Table 1376. Compounds of formula I.17 wherein R¹ is Y-6B and R² is c-C₃H₅.

Table 1377. Compounds of formula I.17 wherein R¹ is Y-7A and R² is c-C₃H₅.

Table 1378. Compounds of formula I.17 wherein R¹ is Y-7B and R² is c-C₃H₅.

Table 1379. Compounds of formula I.17 wherein R¹ is Y-8A and R² is c-C₃H₅.

Table 1380. Compounds of formula I.17 wherein R¹ is Y-8B and R² is c-C₃H₅.

Table 1381. Compounds of formula I.18 wherein R¹ is Y-1A and R² is H.

Table 1382. Compounds of formula I.18 wherein R¹ is Y-1B and R² is H.

Table 1383. Compounds of formula I.18 wherein R¹ is Y-2A and R² is H.

Table 1384. Compounds of formula I.18 wherein R¹ is Y-2B and R² is H.

Table 1385. Compounds of formula I.18 wherein R¹ is Y-3A and R² is H.

Table 1386. Compounds of formula I.18 wherein R¹ is Y-3B and R² is H.

Table 1387. Compounds of formula I.18 wherein R¹ is Y-3C and R² is H.

Table 1388. Compounds of formula I.18 wherein R¹ is Y-3D and R² is H.

Table 1389. Compounds of formula I.18 wherein R¹ is Y-4A and R² is H.

Table 1390. Compounds of formula I.18 wherein R¹ is Y-4B and R² is H.

Table 1391. Compounds of formula I.18 wherein R¹ is Y-4C and R² is H.

Table 1392. Compounds of formula I.18 wherein R¹ is Y-4D and R² is H.

Table 1393. Compounds of formula I.18 wherein R¹ is Y-5A and R² is H.

Table 1394. Compounds of formula I.18 wherein R¹ is Y-5B and R² is H.

Table 1395. Compounds of formula I.18 wherein R¹ is Y-6A and R² is H.

Table 1396. Compounds of formula I.18 wherein R¹ is Y-6B and R² is H.

Table 1397. Compounds of formula I.18 wherein R¹ is Y-7A and R² is H.

Table 1398. Compounds of formula I.18 wherein R¹ is Y-7B and R² is H.

Table 1399. Compounds of formula I.18 wherein R¹ is Y-8A and R² is H.

Table 1400. Compounds of formula I.18 wherein R¹ is Y-8B and R² is H.

Table 1401. Compounds of formula I.18 wherein R¹ is Y-1A and R² is CH₃.

Table 1402. Compounds of formula I.18 wherein R¹ is Y-1B and R² is CH₃.

Table 1403. Compounds of formula I.18 wherein R¹ is Y-2A and R² is CH₃.

Table 1404. Compounds of formula I.18 wherein R¹ is Y-2B and R² is CH₃.

Table 1405. Compounds of formula I.18 wherein R¹ is Y-3A and R² is CH₃.

Table 1406. Compounds of formula I.18 wherein R¹ is Y-3B and R² is CH₃.

Table 1407. Compounds of formula I.18 wherein R¹ is Y-3C and R² is CH₃.

Table 1408. Compounds of formula I.18 wherein R¹ is Y-3D and R² is CH₃.

Table 1409. Compounds of formula I.18 wherein R¹ is Y-4A and R² is CH₃.

Table 1410. Compounds of formula I.18 wherein R¹ is Y-4B and R² is CH₃.

Table 1411. Compounds of formula I.18 wherein R¹ is Y-4C and R² is CH₃.

Table 1412. Compounds of formula I.18 wherein R¹ is Y-4D and R² is CH₃.

Table 1413. Compounds of formula I.18 wherein R¹ is Y-5A and R² is CH₃.

Table 1414. Compounds of formula I.18 wherein R¹ is Y-5B and R² is CH₃.

Table 1415. Compounds of formula I.18 wherein R¹ is Y-6A and R² is CH₃.

Table 1416. Compounds of formula I.18 wherein R¹ is Y-6B and R² is CH₃.

Table 1417. Compounds of formula I.18 wherein R¹ is Y-7A and R² is CH₃.

Table 1418. Compounds of formula I.18 wherein R¹ is Y-7B and R² is CH₃.

Table 1419. Compounds of formula I.18 wherein R¹ is Y-8A and R² is CH₃.

Table 1420. Compounds of formula I.18 wherein R¹ is Y-8B and R² is CH₃.

Table 1421. Compounds of formula I.18 wherein R¹ is Y-1A and R² is c-C₃H₅.

Table 1422. Compounds of formula I.18 wherein R¹ is Y-1B and R² is c-C₃H₅.

Table 1423. Compounds of formula I.18 wherein R¹ is Y-2A and R² is c-C₃H₅.

Table 1424. Compounds of formula I.18 wherein R¹ is Y-2B and R² is c-C₃H₅.

Table 1425. Compounds of formula I.18 wherein R¹ is Y-3A and R² is c-C₃H₅.

Table 1426. Compounds of formula I.18 wherein R¹ is Y-3B and R² is c-C₃H₅.

Table 1427. Compounds of formula I.18 wherein R¹ is Y-3C and R² is c-C₃H₅.

Table 1428. Compounds of formula I.18 wherein R¹ is Y-3D and R² is c-C₃H₅.

Table 1429. Compounds of formula I.18 wherein R¹ is Y-4A and R² is c-C₃H₅.

Table 1430. Compounds of formula I.18 wherein R¹ is Y-4B and R² is c-C₃H₅.

Table 1431. Compounds of formula I.18 wherein R¹ is Y-4C and R² is c-C₃H₅.

Table 1432. Compounds of formula I.18 wherein R¹ is Y-4D and R² is c-C₃H₅.

Table 1433. Compounds of formula I.18 wherein R¹ is Y-5A and R² is c-C₃H₅.

Table 1434. Compounds of formula I.18 wherein R¹ is Y-5B and R² is c-C₃H₅.

Table 1435. Compounds of formula I.18 wherein R¹ is Y-6A and R² is c-C₃H₅.

Table 1436. Compounds of formula I.18 wherein R¹ is Y-6B and R² is c-C₃H₅.

Table 1437. Compounds of formula I.18 wherein R¹ is Y-7A and R² is c-C₃H₅.

Table 1438. Compounds of formula I.18 wherein R¹ is Y-7B and R² is c-C₃H₅.

Table 1439. Compounds of formula I.18 wherein R¹ is Y-8A and R² is c-C₃H₅.

Table 1440. Compounds of formula I.18 wherein R¹ is Y-8B and R² is c-C₃H₅.

TABLE B Abbreviations used in Table B are NH ═N1, NCH₃═N2, and NC₂H₅ ═N3 Line W B¹ B² B³ Ar D 1 N1 CH CH CH Ar¹ R¹¹-1 2 N1 CH CH CH Ar¹ R¹¹-2 3 N1 CH CH CH Ar¹ R¹¹-3 4 N1 CH CH CH Ar¹ R¹¹-5 5 N1 CH CH CH Ar¹ R¹¹-6 6 N1 CH CH CH Ar¹ R¹¹-7 7 N1 CH CH CH Ar¹ R¹¹-8 8 N1 CH CH CH Ar¹ R¹¹-9 9 N1 CH CH CH Ar¹ R¹¹-10 10 N1 CH CH CH Ar¹ R¹¹-11 11 N1 CH CH CH Ar¹ R¹¹-12 12 N1 CH CH CH Ar¹ R¹¹-13 13 N1 CH CH CH Ar¹ R¹¹-14 14 N1 CH CH CH Ar¹ R¹¹-15 15 N1 CH CH CH Ar¹ R¹¹-16 16 N1 CH CH CH Ar¹ R¹¹-17 17 N1 CH CH CH Ar¹ R¹¹-18 18 N1 CH CH CH Ar¹ R¹¹-19 19 N1 CH CH CH Ar¹ R¹¹-20 20 N1 CH CH CH Ar¹ R¹¹-21 21 N1 CH CH CH Ar¹ R¹¹-22 22 N1 CH CH CH Ar¹ R¹¹-23 23 N1 CH CH CH Ar¹ R¹¹-25 24 N1 CH CH CH Ar¹ R¹¹-26 25 N1 CH CH CH Ar¹ R¹¹-27 26 N1 CH CH CH Ar¹ R¹¹-28 27 N1 CH CH CH Ar¹ R¹¹-29 28 N1 CH CH CH Ar¹ A¹¹-1 29 N1 CH CH CH Ar¹ A¹¹-2 30 N1 CH CH CH Ar¹ A¹¹-3 31 N1 CH CH CH Ar² R¹¹-1 32 N1 CH CH CH Ar² R¹¹-2 33 N1 CH CH CH Ar² R¹¹-3 34 N1 CH CH CH Ar² R¹¹-5 35 N1 CH CH CH Ar² R¹¹-6 36 N1 CH CH CH Ar² R¹¹-7 37 N1 CH CH CH Ar² R¹¹-8 38 N1 CH CH CH Ar² R¹¹-9 39 N1 CH CH CH Ar² R¹¹-10 40 N1 CH CH CH Ar² R¹¹-11 41 N1 CH CH CH Ar² R¹¹-12 42 N1 CH CH CH Ar² R¹¹-13 43 N1 CH CH CH Ar² R¹¹-14 44 N1 CH CH CH Ar² R¹¹-15 45 N1 CH CH CH Ar² R¹¹-16 46 N1 CH CH CH Ar² R¹¹-17 47 N1 CH CH CH Ar² R¹¹-18 48 N1 CH CH CH Ar² R¹¹-19 49 N1 CH CH CH Ar² R¹¹-20 50 N1 CH CH CH Ar² R¹¹-21 51 N1 CH CH CH Ar² R¹¹-22 52 N1 CH CH CH Ar² R¹¹-23 53 N1 CH CH CH Ar² R¹¹-25 54 N1 CH CH CH Ar² R¹¹-26 55 N1 CH CH CH Ar² R¹¹-27 56 N1 CH CH CH Ar² R¹¹-28 57 N1 CH CH CH Ar² R¹¹-29 58 N1 CH CH CH Ar² A¹¹-1 59 N1 CH CH CH Ar² A¹¹-2 60 N1 CH CH CH Ar² A¹¹-3 61 N1 CH CH CH Ar³ R¹¹-1 62 N1 CH CH CH Ar³ R¹¹-2 63 N1 CH CH CH Ar³ R¹¹-3 64 N1 CH CH CH Ar³ R¹¹-5 65 N1 CH CH CH Ar³ R¹¹-6 66 N1 CH CH CH Ar³ R¹¹-7 67 N1 CH CH CH Ar³ R¹¹-8 68 N1 CH CH CH Ar³ R¹¹-9 69 N1 CH CH CH Ar³ R¹¹-10 70 N1 CH CH CH Ar³ R¹¹-11 71 N1 CH CH CH Ar³ R¹¹-12 72 N1 CH CH CH Ar³ R¹¹-13 73 N1 CH CH CH Ar³ R¹¹-14 74 N1 CH CH CH Ar³ R¹¹-15 75 N1 CH CH CH Ar³ R¹¹-16 76 N1 CH CH CH Ar³ R¹¹-17 77 N1 CH CH CH Ar³ R¹¹-18 78 N1 CH CH CH Ar³ R¹¹-19 79 N1 CH CH CH Ar³ R¹¹-20 80 N1 CH CH CH Ar³ R¹¹-21 81 N1 CH CH CH Ar³ R¹¹-22 82 N1 CH CH CH Ar³ R¹¹-23 83 N1 CH CH CH Ar³ R¹¹-25 84 N1 CH CH CH Ar³ R¹¹-26 85 N1 CH CH CH Ar³ R¹¹-27 86 N1 CH CH CH Ar³ R¹¹-28 87 N1 CH CH CH Ar³ R¹¹-29 88 N1 CH CH CH Ar³ A¹¹-1 89 N1 CH CH CH Ar³ A¹¹-2 90 N1 CH CH CH Ar³ A¹¹-3 91 N1 CH CH CH Ar⁴ R¹¹-1 92 N1 CH CH CH Ar⁴ R¹¹-2 93 N1 CH CH CH Ar⁴ R¹¹-3 94 N1 CH CH CH Ar⁴ R¹¹-5 95 N1 CH CH CH Ar⁴ R¹¹-6 96 N1 CH CH CH Ar⁴ R¹¹-7 97 N1 CH CH CH Ar⁴ R¹¹-8 98 N1 CH CH CH Ar⁴ R¹¹-9 99 N1 CH CH CH Ar⁴ R¹¹-10 100 N1 CH CH CH Ar⁴ R¹¹-11 101 N1 CH CH CH Ar⁴ R¹¹-12 102 N1 CH CH CH Ar⁴ R¹¹-13 103 N1 CH CH CH Ar⁴ R¹¹-14 104 N1 CH CH CH Ar⁴ R¹¹-15 105 N1 CH CH CH Ar⁴ R¹¹-16 106 N1 CH CH CH Ar⁴ R¹¹-17 107 N1 CH CH CH Ar⁴ R¹¹-18 108 N1 CH CH CH Ar⁴ R¹¹-19 109 N1 CH CH CH Ar⁴ R¹¹-20 110 N1 CH CH CH Ar⁴ R¹¹-21 111 N1 CH CH CH Ar⁴ R¹¹-22 112 N1 CH CH CH Ar⁴ R¹¹-23 113 N1 CH CH CH Ar⁴ R¹¹-25 114 N1 CH CH CH Ar⁴ R¹¹-26 115 N1 CH CH CH Ar⁴ R¹¹-27 116 N1 CH CH CH Ar⁴ R¹¹-28 117 N1 CH CH CH Ar⁴ R¹¹-29 118 N1 CH CH CH Ar⁴ A¹¹-1 119 N1 CH CH CH Ar⁴ A¹¹-2 120 N1 CH CH CH Ar⁴ A¹¹-3 121 N1 CH CH CH Ar¹⁰ R¹¹-1 122 N1 CH CH CH Ar¹⁰ R¹¹-2 123 N1 CH CH CH Ar¹⁰ R¹¹-3 124 N1 CH CH CH Ar¹⁰ R¹¹-5 125 N1 CH CH CH Ar¹⁰ R¹¹-6 126 N1 CH CH CH Ar¹⁰ R¹¹-7 127 N1 CH CH CH Ar¹⁰ R¹¹-8 128 N1 CH CH CH Ar¹⁰ R¹¹-9 129 N1 CH CH CH Ar¹⁰ R¹¹-10 130 N1 CH CH CH Ar¹⁰ R¹¹-11 131 N1 CH CH CH Ar¹⁰ R¹¹-12 132 N1 CH CH CH Ar¹⁰ R¹¹-13 133 N1 CH CH CH Ar¹⁰ R¹¹-14 134 N1 CH CH CH Ar¹⁰ R¹¹-15 135 N1 CH CH CH Ar¹⁰ R¹¹-16 136 N1 CH CH CH Ar¹⁰ R¹¹-17 137 N1 CH CH CH Ar¹⁰ R¹¹-18 138 N1 CH CH CH Ar¹⁰ R¹¹-19 139 N1 CH CH CH Ar¹⁰ R¹¹-20 140 N1 CH CH CH Ar¹⁰ R¹¹-21 141 N1 CH CH CH Ar¹⁰ R¹¹-22 142 N1 CH CH CH Ar¹⁰ R¹¹-23 143 N1 CH CH CH Ar¹⁰ R¹¹-25 144 N1 CH CH CH Ar¹⁰ R¹¹-26 145 N1 CH CH CH Ar¹⁰ R¹¹-27 146 N1 CH CH CH Ar¹⁰ R¹¹-28 147 N1 CH CH CH Ar¹⁰ R¹¹-29 148 N1 CH CH CH Ar¹⁰ A¹¹-1 149 N1 CH CH CH Ar¹⁰ A¹¹-2 150 N1 CH CH CH Ar¹⁰ A¹¹-3 151 N1 CH CH CH Ar¹⁷ R¹¹-1 152 N1 CH CH CH Ar¹⁷ R¹¹-2 153 N1 CH CH CH Ar¹⁷ R¹¹-3 154 N1 CH CH CH Ar¹⁷ R¹¹-5 155 N1 CH CH CH Ar¹⁷ R¹¹-6 156 N1 CH CH CH Ar¹⁷ R¹¹-7 157 N1 CH CH CH Ar¹⁷ R¹¹-8 158 N1 CH CH CH Ar¹⁷ R¹¹-9 159 N1 CH CH CH Ar¹⁷ R¹¹-10 160 N1 CH CH CH Ar¹⁷ R¹¹-11 161 N1 CH CH CH Ar¹⁷ R¹¹-12 162 N1 CH CH CH Ar¹⁷ R¹¹-13 163 N1 CH CH CH Ar¹⁷ R¹¹-14 164 N1 CH CH CH Ar¹⁷ R¹¹-15 165 N1 CH CH CH Ar¹⁷ R¹¹-16 166 N1 CH CH CH Ar¹⁷ R¹¹-17 167 N1 CH CH CH Ar¹⁷ R¹¹-18 168 N1 CH CH CH Ar¹⁷ R¹¹-19 169 N1 CH CH CH Ar¹⁷ R¹¹-20 170 N1 CH CH CH Ar¹⁷ R¹¹-21 171 N1 CH CH CH Ar¹⁷ R¹¹-22 172 N1 CH CH CH Ar¹⁷ R¹¹-23 173 N1 CH CH CH Ar¹⁷ R¹¹-25 174 N1 CH CH CH Ar¹⁷ R¹¹-26 175 N1 CH CH CH Ar¹⁷ R¹¹-27 176 N1 CH CH CH Ar¹⁷ R¹¹-28 177 N1 CH CH CH Ar¹⁷ R¹¹-29 178 N1 CH CH CH Ar¹⁷ A¹¹-1 179 N1 CH CH CH Ar¹⁷ A¹¹-2 180 N1 CH CH CH Ar¹⁷ A¹¹-3 181 N1 CH CH CH Ar¹⁸ R¹¹-1 182 N1 CH CH CH Ar¹⁸ R¹¹-2 183 N1 CH CH CH Ar¹⁸ R¹¹-3 184 N1 CH CH CH Ar¹⁸ R¹¹-5 185 N1 CH CH CH Ar¹⁸ R¹¹-6 186 N1 CH CH CH Ar¹⁸ R¹¹-7 187 N1 CH CH CH Ar¹⁸ R¹¹-8 188 N1 CH CH CH Ar¹⁸ R¹¹-9 189 N1 CH CH CH Ar¹⁸ R¹¹-10 190 N1 CH CH CH Ar¹⁸ R¹¹-11 191 N1 CH CH CH Ar¹⁸ R¹¹-12 192 N1 CH CH CH Ar¹⁸ R¹¹-13 193 N1 CH CH CH Ar¹⁸ R¹¹-14 194 N1 CH CH CH Ar¹⁸ R¹¹-15 195 N1 CH CH CH Ar¹⁸ R¹¹-16 196 N1 CH CH CH Ar¹⁸ R¹¹-17 197 N1 CH CH CH Ar¹⁸ R¹¹-18 198 N1 CH CH CH Ar¹⁸ R¹¹-19 199 N1 CH CH CH Ar¹⁸ R¹¹-20 200 N1 CH CH CH Ar¹⁸ R¹¹-21 201 N1 CH CH CH Ar¹⁸ R¹¹-22 202 N1 CH CH CH Ar¹⁸ R¹¹-23 203 N1 CH CH CH Ar¹⁸ R¹¹-25 204 N1 CH CH CH Ar¹⁸ R¹¹-26 205 N1 CH CH CH Ar¹⁸ R¹¹-27 206 N1 CH CH CH Ar¹⁸ R¹¹-28 207 N1 CH CH CH Ar¹⁸ R¹¹-29 208 N1 CH CH CH Ar¹⁸ A¹¹-1 209 N1 CH CH CH Ar¹⁸ A¹¹-2 210 N1 CH CH CH Ar¹⁸ A¹¹-3 211 N2 CH CH CH Ar¹ R¹¹-1 212 N2 CH CH CH Ar¹ R¹¹-2 213 N2 CH CH CH Ar¹ R¹¹-3 214 N2 CH CH CH Ar¹ R¹¹-5 215 N2 CH CH CH Ar¹ R¹¹-6 216 N2 CH CH CH Ar¹ R¹¹-7 217 N2 CH CH CH Ar¹ R¹¹-8 218 N2 CH CH CH Ar¹ R¹¹-9 219 N2 CH CH CH Ar¹ R¹¹-10 220 N2 CH CH CH Ar¹ R¹¹-11 221 N2 CH CH CH Ar¹ R¹¹-12 222 N2 CH CH CH Ar¹ R¹¹-13 223 N2 CH CH CH Ar¹ R¹¹-14 224 N2 CH CH CH Ar¹ R¹¹-15 225 N2 CH CH CH Ar¹ R¹¹-16 226 N2 CH CH CH Ar¹ R¹¹-17 227 N2 CH CH CH Ar¹ R¹¹-18 228 N2 CH CH CH Ar¹ R¹¹-19 229 N2 CH CH CH Ar¹ R¹¹-20 230 N2 CH CH CH Ar¹ R¹¹-21 231 N2 CH CH CH Ar¹ R¹¹-22 232 N2 CH CH CH Ar¹ R¹¹-23 233 N2 CH CH CH Ar¹ R¹¹-25 234 N2 CH CH CH Ar¹ R¹¹-26 235 N2 CH CH CH Ar¹ R¹¹-27 236 N2 CH CH CH Ar¹ R¹¹-28 237 N2 CH CH CH Ar¹ R¹¹-29 238 N2 CH CH CH Ar¹ A¹¹-1 239 N2 CH CH CH Ar¹ A¹¹-2 240 N2 CH CH CH Ar¹ A¹¹-3 241 N2 CH CH CH Ar² R¹¹-1 242 N2 CH CH CH Ar² R¹¹-2 243 N2 CH CH CH Ar² R¹¹-3 244 N2 CH CH CH Ar² R¹¹-5 245 N2 CH CH CH Ar² R¹¹-6 246 N2 CH CH CH Ar² R¹¹-7 247 N2 CH CH CH Ar² R¹¹-8 248 N2 CH CH CH Ar² R¹¹-9 249 N2 CH CH CH Ar² R¹¹-10 250 N2 CH CH CH Ar² R¹¹-11 251 N2 CH CH CH Ar² R¹¹-12 252 N2 CH CH CH Ar² R¹¹-13 253 N2 CH CH CH Ar² R¹¹-14 254 N2 CH CH CH Ar² R¹¹-15 255 N2 CH CH CH Ar² R¹¹-16 256 N2 CH CH CH Ar² R¹¹-17 257 N2 CH CH CH Ar² R¹¹-18 258 N2 CH CH CH Ar² R¹¹-19 259 N2 CH CH CH Ar² R¹¹-20 260 N2 CH CH CH Ar² R¹¹-21 261 N2 CH CH CH Ar² R¹¹-22 262 N2 CH CH CH Ar² R¹¹-23 263 N2 CH CH CH Ar² R¹¹-25 264 N2 CH CH CH Ar² R¹¹-26 265 N2 CH CH CH Ar² R¹¹-27 266 N2 CH CH CH Ar² R¹¹-28 267 N2 CH CH CH Ar² R¹¹-29 268 N2 CH CH CH Ar² A¹¹-1 269 N2 CH CH CH Ar² A¹¹-2 270 N2 CH CH CH Ar² A¹¹-3 271 N2 CH CH CH Ar³ R¹¹-1 272 N2 CH CH CH Ar³ R¹¹-2 273 N2 CH CH CH Ar³ R¹¹-3 274 N2 CH CH CH Ar³ R¹¹-5 275 N2 CH CH CH Ar³ R¹¹-6 276 N2 CH CH CH Ar³ R¹¹-7 277 N2 CH CH CH Ar³ R¹¹-8 278 N2 CH CH CH Ar³ R¹¹-9 279 N2 CH CH CH Ar³ R¹¹-10 280 N2 CH CH CH Ar³ R¹¹-11 281 N2 CH CH CH Ar³ R¹¹-12 282 N2 CH CH CH Ar³ R¹¹-13 283 N2 CH CH CH Ar³ R¹¹-14 284 N2 CH CH CH Ar³ R¹¹-15 285 N2 CH CH CH Ar³ R¹¹-16 286 N2 CH CH CH Ar³ R¹¹-17 287 N2 CH CH CH Ar³ R¹¹-18 288 N2 CH CH CH Ar³ R¹¹-19 289 N2 CH CH CH Ar³ R¹¹-20 290 N2 CH CH CH Ar³ R¹¹-21 291 N2 CH CH CH Ar³ R¹¹-22 292 N2 CH CH CH Ar³ R¹¹-23 293 N2 CH CH CH Ar³ R¹¹-25 294 N2 CH CH CH Ar³ R¹¹-26 295 N2 CH CH CH Ar³ R¹¹-27 296 N2 CH CH CH Ar³ R¹¹-28 297 N2 CH CH CH Ar³ R¹¹-29 298 N2 CH CH CH Ar³ A¹¹-1 299 N2 CH CH CH Ar³ A¹¹-2 300 N2 CH CH CH Ar³ A¹¹-3 301 N2 CH CH CH Ar⁴ R¹¹-1 302 N2 CH CH CH Ar⁴ R¹¹-2 303 N2 CH CH CH Ar⁴ R¹¹-3 304 N2 CH CH CH Ar⁴ R¹¹-5 305 N2 CH CH CH Ar⁴ R¹¹-6 306 N2 CH CH CH Ar⁴ R¹¹-7 307 N2 CH CH CH Ar⁴ R¹¹-8 308 N2 CH CH CH Ar⁴ R¹¹-9 309 N2 CH CH CH Ar⁴ R¹¹-10 310 N2 CH CH CH Ar⁴ R¹¹-11 311 N2 CH CH CH Ar⁴ R¹¹-12 312 N2 CH CH CH Ar⁴ R¹¹-13 313 N2 CH CH CH Ar⁴ R¹¹-14 314 N2 CH CH CH Ar⁴ R¹¹-15 315 N2 CH CH CH Ar⁴ R¹¹-16 316 N2 CH CH CH Ar⁴ R¹¹-17 317 N2 CH CH CH Ar⁴ R¹¹-18 318 N2 CH CH CH Ar⁴ R¹¹-19 319 N2 CH CH CH Ar⁴ R¹¹-20 320 N2 CH CH CH Ar⁴ R¹¹-21 321 N2 CH CH CH Ar⁴ R¹¹-22 322 N2 CH CH CH Ar⁴ R¹¹-23 323 N2 CH CH CH Ar⁴ R¹¹-25 324 N2 CH CH CH Ar⁴ R¹¹-26 325 N2 CH CH CH Ar⁴ R¹¹-27 326 N2 CH CH CH Ar⁴ R¹¹-28 327 N2 CH CH CH Ar⁴ R¹¹-29 328 N2 CH CH CH Ar⁴ A¹¹-1 329 N2 CH CH CH Ar⁴ A¹¹-2 330 N2 CH CH CH Ar⁴ A¹¹-3 331 N2 CH CH CH Ar¹⁰ R¹¹-1 332 N2 CH CH CH Ar¹⁰ R¹¹-2 333 N2 CH CH CH Ar¹⁰ R¹¹-3 334 N2 CH CH CH Ar¹⁰ R¹¹-5 335 N2 CH CH CH Ar¹⁰ R¹¹-6 336 N2 CH CH CH Ar¹⁰ R¹¹-7 337 N2 CH CH CH Ar¹⁰ R¹¹-8 338 N2 CH CH CH Ar¹⁰ R¹¹-9 339 N2 CH CH CH Ar¹⁰ R¹¹-10 340 N2 CH CH CH Ar¹⁰ R¹¹-11 341 N2 CH CH CH Ar¹⁰ R¹¹-12 342 N2 CH CH CH Ar¹⁰ R¹¹-13 343 N2 CH CH CH Ar¹⁰ R¹¹-14 344 N2 CH CH CH Ar¹⁰ R¹¹-15 345 N2 CH CH CH Ar¹⁰ R¹¹-16 346 N2 CH CH CH Ar¹⁰ R¹¹-17 347 N2 CH CH CH Ar¹⁰ R¹¹-18 348 N2 CH CH CH Ar¹⁰ R¹¹-19 349 N2 CH CH CH Ar¹⁰ R¹¹-20 350 N2 CH CH CH Ar¹⁰ R¹¹-21 351 N2 CH CH CH Ar¹⁰ R¹¹-22 352 N2 CH CH CH Ar¹⁰ R¹¹-23 353 N2 CH CH CH Ar¹⁰ R¹¹-25 354 N2 CH CH CH Ar¹⁰ R¹¹-26 355 N2 CH CH CH Ar¹⁰ R¹¹-27 356 N2 CH CH CH Ar¹⁰ R¹¹-28 357 N2 CH CH CH Ar¹⁰ R¹¹-29 358 N2 CH CH CH Ar¹⁰ A¹¹-1 359 N2 CH CH CH Ar¹⁰ A¹¹-2 360 N2 CH CH CH Ar¹⁰ A¹¹-3 361 N2 CH CH CH Ar¹⁷ R¹¹-1 362 N2 CH CH CH Ar¹⁷ R¹¹-2 363 N2 CH CH CH Ar¹⁷ R¹¹-3 364 N2 CH CH CH Ar¹⁷ R¹¹-5 365 N2 CH CH CH Ar¹⁷ R¹¹-6 366 N2 CH CH CH Ar¹⁷ R¹¹-7 367 N2 CH CH CH Ar¹⁷ R¹¹-8 368 N2 CH CH CH Ar¹⁷ R¹¹-9 369 N2 CH CH CH Ar¹⁷ R¹¹-10 370 N2 CH CH CH Ar¹⁷ R¹¹-11 371 N2 CH CH CH Ar¹⁷ R¹¹-12 372 N2 CH CH CH Ar¹⁷ R¹¹-13 373 N2 CH CH CH Ar¹⁷ R¹¹-14 374 N2 CH CH CH Ar¹⁷ R¹¹-15 375 N2 CH CH CH Ar¹⁷ R¹¹-16 376 N2 CH CH CH Ar¹⁷ R¹¹-17 377 N2 CH CH CH Ar¹⁷ R¹¹-18 378 N2 CH CH CH Ar¹⁷ R¹¹-19 379 N2 CH CH CH Ar¹⁷ R¹¹-20 380 N2 CH CH CH Ar¹⁷ R¹¹-21 381 N2 CH CH CH Ar¹⁷ R¹¹-22 382 N2 CH CH CH Ar¹⁷ R¹¹-23 383 N2 CH CH CH Ar¹⁷ R¹¹-25 384 N2 CH CH CH Ar¹⁷ R¹¹-26 385 N2 CH CH CH Ar¹⁷ R¹¹-27 386 N2 CH CH CH Ar¹⁷ R¹¹-28 387 N2 CH CH CH Ar¹⁷ R¹¹-29 388 N2 CH CH CH Ar¹⁷ A¹¹-1 389 N2 CH CH CH Ar¹⁷ A¹¹-2 390 N2 CH CH CH Ar¹⁷ A¹¹-3 391 N2 CH CH CH Ar¹⁸ R¹¹-1 392 N2 CH CH CH Ar¹⁸ R¹¹-2 393 N2 CH CH CH Ar¹⁸ R¹¹-3 394 N2 CH CH CH Ar¹⁸ R¹¹-5 395 N2 CH CH CH Ar¹⁸ R¹¹-6 396 N2 CH CH CH Ar¹⁸ R¹¹-7 397 N2 CH CH CH Ar¹⁸ R¹¹-8 398 N2 CH CH CH Ar¹⁸ R¹¹-9 399 N2 CH CH CH Ar¹⁸ R¹¹-10 400 N2 CH CH CH Ar¹⁸ R¹¹-11 401 N2 CH CH CH Ar¹⁸ R¹¹-12 402 N2 CH CH CH Ar¹⁸ R¹¹-13 403 N2 CH CH CH Ar¹⁸ R¹¹-14 404 N2 CH CH CH Ar¹⁸ R¹¹-15 405 N2 CH CH CH Ar¹⁸ R¹¹-16 406 N2 CH CH CH Ar¹⁸ R¹¹-17 407 N2 CH CH CH Ar¹⁸ R¹¹-18 408 N2 CH CH CH Ar¹⁸ R¹¹-19 409 N2 CH CH CH Ar¹⁸ R¹¹-20 410 N2 CH CH CH Ar¹⁸ R¹¹-21 411 N2 CH CH CH Ar¹⁸ R¹¹-22 412 N2 CH CH CH Ar¹⁸ R¹¹-23 413 N2 CH CH CH Ar¹⁸ R¹¹-25 414 N2 CH CH CH Ar¹⁸ R¹¹-26 415 N2 CH CH CH Ar¹⁸ R¹¹-27 416 N2 CH CH CH Ar¹⁸ R¹¹-28 417 N2 CH CH CH Ar¹⁸ R¹¹-29 418 N2 CH CH CH Ar¹⁸ A¹¹-1 419 N2 CH CH CH Ar¹⁸ A¹¹-2 420 N2 CH CH CH Ar¹⁸ A¹¹-3 421 N3 CH CH CH Ar¹ R¹¹-1 422 N3 CH CH CH Ar¹ R¹¹-2 423 N3 CH CH CH Ar¹ R¹¹-3 424 N3 CH CH CH Ar¹ R¹¹-5 425 N3 CH CH CH Ar¹ R¹¹-6 426 N3 CH CH CH Ar¹ R¹¹-7 427 N3 CH CH CH Ar¹ R¹¹-8 428 N3 CH CH CH Ar¹ R¹¹-9 429 N3 CH CH CH Ar¹ R¹¹-10 430 N3 CH CH CH Ar¹ R¹¹-11 431 N3 CH CH CH Ar¹ R¹¹-12 432 N3 CH CH CH Ar¹ R¹¹-13 433 N3 CH CH CH Ar¹ R¹¹-14 434 N3 CH CH CH Ar¹ R¹¹-15 435 N3 CH CH CH Ar¹ R¹¹-16 436 N3 CH CH CH Ar¹ R¹¹-17 437 N3 CH CH CH Ar¹ R¹¹-18 438 N3 CH CH CH Ar¹ R¹¹-19 439 N3 CH CH CH Ar¹ R¹¹-20 440 N3 CH CH CH Ar¹ R¹¹-21 441 N3 CH CH CH Ar¹ R¹¹-22 442 N3 CH CH CH Ar¹ R¹¹-23 443 N3 CH CH CH Ar¹ R¹¹-25 444 N3 CH CH CH Ar¹ R¹¹-26 445 N3 CH CH CH Ar¹ R¹¹-27 446 N3 CH CH CH Ar¹ R¹¹-28 447 N3 CH CH CH Ar¹ R¹¹-29 448 N3 CH CH CH Ar¹ A¹¹-1 449 N3 CH CH CH Ar¹ A¹¹-2 450 N3 CH CH CH Ar¹ A¹¹-3 451 N3 CH CH CH Ar² R¹¹-1 452 N3 CH CH CH Ar² R¹¹-2 453 N3 CH CH CH Ar² R¹¹-3 454 N3 CH CH CH Ar² R¹¹-5 455 N3 CH CH CH Ar² R¹¹-6 456 N3 CH CH CH Ar² R¹¹-7 457 N3 CH CH CH Ar² R¹¹-8 458 N3 CH CH CH Ar² R¹¹-9 459 N3 CH CH CH Ar² R¹¹-10 460 N3 CH CH CH Ar² R¹¹-11 461 N3 CH CH CH Ar² R¹¹-12 462 N3 CH CH CH Ar² R¹¹-13 463 N3 CH CH CH Ar² R¹¹-14 464 N3 CH CH CH Ar² R¹¹-15 465 N3 CH CH CH Ar² R¹¹-16 466 N3 CH CH CH Ar² R¹¹-17 467 N3 CH CH CH Ar² R¹¹-18 468 N3 CH CH CH Ar² R¹¹-19 469 N3 CH CH CH Ar² R¹¹-20 470 N3 CH CH CH Ar² R¹¹-21 471 N3 CH CH CH Ar² R¹¹-22 472 N3 CH CH CH Ar² R¹¹-23 473 N3 CH CH CH Ar² R¹¹-25 474 N3 CH CH CH Ar² R¹¹-26 475 N3 CH CH CH Ar² R¹¹-27 476 N3 CH CH CH Ar² R¹¹-28 477 N3 CH CH CH Ar² R¹¹-29 478 N3 CH CH CH Ar² A¹¹-1 479 N3 CH CH CH Ar² A¹¹-2 480 N3 CH CH CH Ar² A¹¹-3 481 N3 CH CH CH Ar³ R¹¹-1 482 N3 CH CH CH Ar³ R¹¹-2 483 N3 CH CH CH Ar³ R¹¹-3 484 N3 CH CH CH Ar³ R¹¹-5 485 N3 CH CH CH Ar³ R¹¹-6 486 N3 CH CH CH Ar³ R¹¹-7 487 N3 CH CH CH Ar³ R¹¹-8 488 N3 CH CH CH Ar³ R¹¹-9 489 N3 CH CH CH Ar³ R¹¹-10 490 N3 CH CH CH Ar³ R¹¹-11 491 N3 CH CH CH Ar³ R¹¹-12 492 N3 CH CH CH Ar³ R¹¹-13 493 N3 CH CH CH Ar³ R¹¹-14 494 N3 CH CH CH Ar³ R¹¹-15 495 N3 CH CH CH Ar³ R¹¹-16 496 N3 CH CH CH Ar³ R¹¹-17 497 N3 CH CH CH Ar³ R¹¹-18 498 N3 CH CH CH Ar³ R¹¹-19 499 N3 CH CH CH Ar³ R¹¹-20 500 N3 CH CH CH Ar³ R¹¹-21 501 N3 CH CH CH Ar³ R¹¹-22 502 N3 CH CH CH Ar³ R¹¹-23 503 N3 CH CH CH Ar³ R¹¹-25 504 N3 CH CH CH Ar³ R¹¹-26 505 N3 CH CH CH Ar³ R¹¹-27 506 N3 CH CH CH Ar³ R¹¹-28 507 N3 CH CH CH Ar³ R¹¹-29 508 N3 CH CH CH Ar³ A¹¹-1 509 N3 CH CH CH Ar³ A¹¹-2 510 N3 CH CH CH Ar³ A¹¹-3 511 N3 CH CH CH Ar⁴ R¹¹-1 512 N3 CH CH CH Ar⁴ R¹¹-2 513 N3 CH CH CH Ar⁴ R¹¹-3 514 N3 CH CH CH Ar⁴ R¹¹-5 515 N3 CH CH CH Ar⁴ R¹¹-6 516 N3 CH CH CH Ar⁴ R¹¹-7 517 N3 CH CH CH Ar⁴ R¹¹-8 518 N3 CH CH CH Ar⁴ R¹¹-9 519 N3 CH CH CH Ar⁴ R¹¹-10 520 N3 CH CH CH Ar⁴ R¹¹-11 521 N3 CH CH CH Ar⁴ R¹¹-12 522 N3 CH CH CH Ar⁴ R¹¹-13 523 N3 CH CH CH Ar⁴ R¹¹-14 524 N3 CH CH CH Ar⁴ R¹¹-15 525 N3 CH CH CH Ar⁴ R¹¹-16 526 N3 CH CH CH Ar⁴ R¹¹-17 527 N3 CH CH CH Ar⁴ R¹¹-18 528 N3 CH CH CH Ar⁴ R¹¹-19 529 N3 CH CH CH Ar⁴ R¹¹-20 530 N3 CH CH CH Ar⁴ R¹¹-21 531 N3 CH CH CH Ar⁴ R¹¹-22 532 N3 CH CH CH Ar⁴ R¹¹-23 533 N3 CH CH CH Ar⁴ R¹¹-25 534 N3 CH CH CH Ar⁴ R¹¹-26 535 N3 CH CH CH Ar⁴ R¹¹-27 536 N3 CH CH CH Ar⁴ R¹¹-28 537 N3 CH CH CH Ar⁴ R¹¹-29 538 N3 CH CH CH Ar⁴ A¹¹-1 539 N3 CH CH CH Ar⁴ A¹¹-2 540 N3 CH CH CH Ar⁴ A¹¹-3 541 N3 CH CH CH Ar¹⁰ R¹¹-1 542 N3 CH CH CH Ar¹⁰ R¹¹-2 543 N3 CH CH CH Ar¹⁰ R¹¹-3 544 N3 CH CH CH Ar¹⁰ R¹¹-5 545 N3 CH CH CH Ar¹⁰ R¹¹-6 546 N3 CH CH CH Ar¹⁰ R¹¹-7 547 N3 CH CH CH Ar¹⁰ R¹¹-8 548 N3 CH CH CH Ar¹⁰ R¹¹-9 549 N3 CH CH CH Ar¹⁰ R¹¹-10 550 N3 CH CH CH Ar¹⁰ R¹¹-11 551 N3 CH CH CH Ar¹⁰ R¹¹-12 552 N3 CH CH CH Ar¹⁰ R¹¹-13 553 N3 CH CH CH Ar¹⁰ R¹¹-14 554 N3 CH CH CH Ar¹⁰ R¹¹-15 555 N3 CH CH CH Ar¹⁰ R¹¹-16 556 N3 CH CH CH Ar¹⁰ R¹¹-17 557 N3 CH CH CH Ar¹⁰ R¹¹-18 558 N3 CH CH CH Ar¹⁰ R¹¹-19 559 N3 CH CH CH Ar¹⁰ R¹¹-20 560 N3 CH CH CH Ar¹⁰ R¹¹-21 561 N3 CH CH CH Ar¹⁰ R¹¹-22 562 N3 CH CH CH Ar¹⁰ R¹¹-23 563 N3 CH CH CH Ar¹⁰ R¹¹-25 564 N3 CH CH CH Ar¹⁰ R¹¹-26 565 N3 CH CH CH Ar¹⁰ R¹¹-27 566 N3 CH CH CH Ar¹⁰ R¹¹-28 567 N3 CH CH CH Ar¹⁰ R¹¹-29 568 N3 CH CH CH Ar¹⁰ A¹¹-1 569 N3 CH CH CH Ar¹⁰ A¹¹-2 570 N3 CH CH CH Ar¹⁰ A¹¹-3 571 N3 CH CH CH Ar¹⁷ R¹¹-1 572 N3 CH CH CH Ar¹⁷ R¹¹-2 573 N3 CH CH CH Ar¹⁷ R¹¹-3 574 N3 CH CH CH Ar¹⁷ R¹¹-5 575 N3 CH CH CH Ar¹⁷ R¹¹-6 576 N3 CH CH CH Ar¹⁷ R¹¹-7 577 N3 CH CH CH Ar¹⁷ R¹¹-8 578 N3 CH CH CH Ar¹⁷ R¹¹-9 579 N3 CH CH CH Ar¹⁷ R¹¹-10 580 N3 CH CH CH Ar¹⁷ R¹¹-11 581 N3 CH CH CH Ar¹⁷ R¹¹-12 582 N3 CH CH CH Ar¹⁷ R¹¹-13 583 N3 CH CH CH Ar¹⁷ R¹¹-14 584 N3 CH CH CH Ar¹⁷ R¹¹-15 585 N3 CH CH CH Ar¹⁷ R¹¹-16 586 N3 CH CH CH Ar¹⁷ R¹¹-17 587 N3 CH CH CH Ar¹⁷ R¹¹-18 588 N3 CH CH CH Ar¹⁷ R¹¹-19 589 N3 CH CH CH Ar¹⁷ R¹¹-20 590 N3 CH CH CH Ar¹⁷ R¹¹-21 591 N3 CH CH CH Ar¹⁷ R¹¹-22 592 N3 CH CH CH Ar¹⁷ R¹¹-23 593 N3 CH CH CH Ar¹⁷ R¹¹-25 594 N3 CH CH CH Ar¹⁷ R¹¹-26 595 N3 CH CH CH Ar¹⁷ R¹¹-27 596 N3 CH CH CH Ar¹⁷ R¹¹-28 597 N3 CH CH CH Ar¹⁷ R¹¹-29 598 N3 CH CH CH Ar¹⁷ A¹¹-1 599 N3 CH CH CH Ar¹⁷ A¹¹-2 600 N3 CH CH CH Ar¹⁷ A¹¹-3 601 N3 CH CH CH Ar¹⁸ R¹¹-1 602 N3 CH CH CH Ar¹⁸ R¹¹-2 603 N3 CH CH CH Ar¹⁸ R¹¹-3 604 N3 CH CH CH Ar¹⁸ R¹¹-5 605 N3 CH CH CH Ar¹⁸ R¹¹-6 606 N3 CH CH CH Ar¹⁸ R¹¹-7 607 N3 CH CH CH Ar¹⁸ R¹¹-8 608 N3 CH CH CH Ar¹⁸ R¹¹-9 609 N3 CH CH CH Ar¹⁸ R¹¹-10 610 N3 CH CH CH Ar¹⁸ R¹¹-11 611 N3 CH CH CH Ar¹⁸ R¹¹-12 612 N3 CH CH CH Ar¹⁸ R¹¹-13 613 N3 CH CH CH Ar¹⁸ R¹¹-14 614 N3 CH CH CH Ar¹⁸ R¹¹-15 615 N3 CH CH CH Ar¹⁸ R¹¹-16 616 N3 CH CH CH Ar¹⁸ R¹¹-17 617 N3 CH CH CH Ar¹⁸ R¹¹-18 618 N3 CH CH CH Ar¹⁸ R¹¹-19 619 N3 CH CH CH Ar¹⁸ R¹¹-20 620 N3 CH CH CH Ar¹⁸ R¹¹-21 621 N3 CH CH CH Ar¹⁸ R¹¹-22 622 N3 CH CH CH Ar¹⁸ R¹¹-23 623 N3 CH CH CH Ar¹⁸ R¹¹-25 624 N3 CH CH CH Ar¹⁸ R¹¹-26 625 N3 CH CH CH Ar¹⁸ R¹¹-27 626 N3 CH CH CH Ar¹⁸ R¹¹-28 627 N3 CH CH CH Ar¹⁸ R¹¹-29 628 N3 CH CH CH Ar¹⁸ A¹¹-1 629 N3 CH CH CH Ar¹⁸ A¹¹-2 630 N3 CH CH CH Ar¹⁸ A¹¹-3 631 O CH CH CH Ar¹ R¹¹-1 632 O CH CH CH Ar¹ R¹¹-2 633 O CH CH CH Ar¹ R¹¹-3 634 O CH CH CH Ar¹ R¹¹-5 635 O CH CH CH Ar¹ R¹¹-6 636 O CH CH CH Ar¹ R¹¹-7 637 O CH CH CH Ar¹ R¹¹-8 638 O CH CH CH Ar¹ R¹¹-9 639 O CH CH CH Ar¹ R¹¹-10 640 O CH CH CH Ar¹ R¹¹-11 641 O CH CH CH Ar¹ R¹¹-12 642 O CH CH CH Ar¹ R¹¹-13 643 O CH CH CH Ar¹ R¹¹-14 644 O CH CH CH Ar¹ R¹¹-15 645 O CH CH CH Ar¹ R¹¹-16 646 O CH CH CH Ar¹ R¹¹-17 647 O CH CH CH Ar¹ R¹¹-18 648 O CH CH CH Ar¹ R¹¹-19 649 O CH CH CH Ar¹ R¹¹-20 650 O CH CH CH Ar¹ R¹¹-21 651 O CH CH CH Ar¹ R¹¹-22 652 O CH CH CH Ar¹ R¹¹-23 653 O CH CH CH Ar¹ R¹¹-25 654 O CH CH CH Ar¹ R¹¹-26 655 O CH CH CH Ar¹ R¹¹-27 656 O CH CH CH Ar¹ R¹¹-28 657 O CH CH CH Ar¹ R¹¹-29 658 O CH CH CH Ar¹ A¹¹-1 659 O CH CH CH Ar¹ A¹¹-2 660 O CH CH CH Ar¹ A¹¹-3 661 O CH CH CH Ar² R¹¹-1 662 O CH CH CH Ar² R¹¹-2 663 O CH CH CH Ar² R¹¹-3 664 O CH CH CH Ar² R¹¹-5 665 O CH CH CH Ar² R¹¹-6 666 O CH CH CH Ar² R¹¹-7 667 O CH CH CH Ar² R¹¹-8 668 O CH CH CH Ar² R¹¹-9 669 O CH CH CH Ar² R¹¹-10 670 O CH CH CH Ar² R¹¹-11 671 O CH CH CH Ar² R¹¹-12 672 O CH CH CH Ar² R¹¹-13 673 O CH CH CH Ar² R¹¹-14 674 O CH CH CH Ar² R¹¹-15 675 O CH CH CH Ar² R¹¹-16 676 O CH CH CH Ar² R¹¹-17 677 O CH CH CH Ar² R¹¹-18 678 O CH CH CH Ar² R¹¹-19 679 O CH CH CH Ar² R¹¹-20 680 O CH CH CH Ar² R¹¹-21 681 O CH CH CH Ar² R¹¹-22 682 O CH CH CH Ar² R¹¹-23 683 O CH CH CH Ar² R¹¹-25 684 O CH CH CH Ar² R¹¹-26 685 O CH CH CH Ar² R¹¹-27 686 O CH CH CH Ar² R¹¹-28 687 O CH CH CH Ar² R¹¹-29 688 O CH CH CH Ar² A¹¹-1 689 O CH CH CH Ar² A¹¹-2 690 O CH CH CH Ar² A¹¹-3 691 O CH CH CH Ar³ R¹¹-1 692 O CH CH CH Ar³ R¹¹-2 693 O CH CH CH Ar³ R¹¹-3 694 O CH CH CH Ar³ R¹¹-5 695 O CH CH CH Ar³ R¹¹-6 696 O CH CH CH Ar³ R¹¹-7 697 O CH CH CH Ar³ R¹¹-8 698 O CH CH CH Ar³ R¹¹-9 699 O CH CH CH Ar³ R¹¹-10 700 O CH CH CH Ar³ R¹¹-11 701 O CH CH CH Ar³ R¹¹-12 702 O CH CH CH Ar³ R¹¹-13 703 O CH CH CH Ar³ R¹¹-14 704 O CH CH CH Ar³ R¹¹-15 705 O CH CH CH Ar³ R¹¹-16 706 O CH CH CH Ar³ R¹¹-17 707 O CH CH CH Ar³ R¹¹-18 708 O CH CH CH Ar³ R¹¹-19 709 O CH CH CH Ar³ R¹¹-20 710 O CH CH CH Ar³ R¹¹-21 711 O CH CH CH Ar³ R¹¹-22 712 O CH CH CH Ar³ R¹¹-23 713 O CH CH CH Ar³ R¹¹-25 714 O CH CH CH Ar³ R¹¹-26 715 O CH CH CH Ar³ R¹¹-27 716 O CH CH CH Ar³ R¹¹-28 717 O CH CH CH Ar³ R¹¹-29 718 O CH CH CH Ar³ A¹¹-1 719 O CH CH CH Ar³ A¹¹-2 720 O CH CH CH Ar³ A¹¹-3 721 O CH CH CH Ar⁴ R¹¹-1 722 O CH CH CH Ar⁴ R¹¹-2 723 O CH CH CH Ar⁴ R¹¹-3 724 O CH CH CH Ar⁴ R¹¹-5 725 O CH CH CH Ar⁴ R¹¹-6 726 O CH CH CH Ar⁴ R¹¹-7 727 O CH CH CH Ar⁴ R¹¹-8 728 O CH CH CH Ar⁴ R¹¹-9 729 O CH CH CH Ar⁴ R¹¹-10 730 O CH CH CH Ar⁴ R¹¹-11 731 O CH CH CH Ar⁴ R¹¹-12 732 O CH CH CH Ar⁴ R¹¹-13 733 O CH CH CH Ar⁴ R¹¹-14 734 O CH CH CH Ar⁴ R¹¹-15 735 O CH CH CH Ar⁴ R¹¹-16 736 O CH CH CH Ar⁴ R¹¹-17 737 O CH CH CH Ar⁴ R¹¹-18 738 O CH CH CH Ar⁴ R¹¹-19 739 O CH CH CH Ar⁴ R¹¹-20 740 O CH CH CH Ar⁴ R¹¹-21 741 O CH CH CH Ar⁴ R¹¹-22 742 O CH CH CH Ar⁴ R¹¹-23 743 O CH CH CH Ar⁴ R¹¹-25 744 O CH CH CH Ar⁴ R¹¹-26 745 O CH CH CH Ar⁴ R¹¹-27 746 O CH CH CH Ar⁴ R¹¹-28 747 O CH CH CH Ar⁴ R¹¹-29 748 O CH CH CH Ar⁴ A¹¹-1 749 O CH CH CH Ar⁴ A¹¹-2 750 O CH CH CH Ar⁴ A¹¹-3 751 O CH CH CH Ar¹⁰ R¹¹-1 752 O CH CH CH Ar¹⁰ R¹¹-2 753 O CH CH CH Ar¹⁰ R¹¹-3 754 O CH CH CH Ar¹⁰ R¹¹-5 755 O CH CH CH Ar¹⁰ R¹¹-6 756 O CH CH CH Ar¹⁰ R¹¹-7 757 O CH CH CH Ar¹⁰ R¹¹-8 758 O CH CH CH Ar¹⁰ R¹¹-9 759 O CH CH CH Ar¹⁰ R¹¹-10 760 O CH CH CH Ar¹⁰ R¹¹-11 761 O CH CH CH Ar¹⁰ R¹¹-12 762 O CH CH CH Ar¹⁰ R¹¹-13 763 O CH CH CH Ar¹⁰ R¹¹-14 764 O CH CH CH Ar¹⁰ R¹¹-15 765 O CH CH CH Ar¹⁰ R¹¹-16 766 O CH CH CH Ar¹⁰ R¹¹-17 767 O CH CH CH Ar¹⁰ R¹¹-18 768 O CH CH CH Ar¹⁰ R¹¹-19 769 O CH CH CH Ar¹⁰ R¹¹-20 770 O CH CH CH Ar¹⁰ R¹¹-21 771 O CH CH CH Ar¹⁰ R¹¹-22 772 O CH CH CH Ar¹⁰ R¹¹-23 773 O CH CH CH Ar¹⁰ R¹¹-25 774 O CH CH CH Ar¹⁰ R¹¹-26 775 O CH CH CH Ar¹⁰ R¹¹-27 776 O CH CH CH Ar¹⁰ R¹¹-28 777 O CH CH CH Ar¹⁰ R¹¹-29 778 O CH CH CH Ar¹⁰ A¹¹-1 779 O CH CH CH Ar¹⁰ A¹¹-2 780 O CH CH CH Ar¹⁰ A¹¹-3 781 O CH CH CH Ar¹⁷ R¹¹-1 782 O CH CH CH Ar¹⁷ R¹¹-2 783 O CH CH CH Ar¹⁷ R¹¹-3 784 O CH CH CH Ar¹⁷ R¹¹-5 785 O CH CH CH Ar¹⁷ R¹¹-6 786 O CH CH CH Ar¹⁷ R¹¹-7 787 O CH CH CH Ar¹⁷ R¹¹-8 788 O CH CH CH Ar¹⁷ R¹¹-9 789 O CH CH CH Ar¹⁷ R¹¹-10 790 O CH CH CH Ar¹⁷ R¹¹-11 791 O CH CH CH Ar¹⁷ R¹¹-12 792 O CH CH CH Ar¹⁷ R¹¹-13 793 O CH CH CH Ar¹⁷ R¹¹-14 794 O CH CH CH Ar¹⁷ R¹¹-15 795 O CH CH CH Ar¹⁷ R¹¹-16 796 O CH CH CH Ar¹⁷ R¹¹-17 797 O CH CH CH Ar¹⁷ R¹¹-18 798 O CH CH CH Ar¹⁷ R¹¹-19 799 O CH CH CH Ar¹⁷ R¹¹-20 800 O CH CH CH Ar¹⁷ R¹¹-21 801 O CH CH CH Ar¹⁷ R¹¹-22 802 O CH CH CH Ar¹⁷ R¹¹-23 803 O CH CH CH Ar¹⁷ R¹¹-25 804 O CH CH CH Ar¹⁷ R¹¹-26 805 O CH CH CH Ar¹⁷ R¹¹-27 806 O CH CH CH Ar¹⁷ R¹¹-28 807 O CH CH CH Ar¹⁷ R¹¹-29 808 O CH CH CH Ar¹⁷ A¹¹-1 809 O CH CH CH Ar¹⁷ A¹¹-2 810 O CH CH CH Ar¹⁷ A¹¹-3 811 O CH CH CH Ar¹⁸ R¹¹-1 812 O CH CH CH Ar¹⁸ R¹¹-2 813 O CH CH CH Ar¹⁸ R¹¹-3 814 O CH CH CH Ar¹⁸ R¹¹-5 815 O CH CH CH Ar¹⁸ R¹¹-6 816 O CH CH CH Ar¹⁸ R¹¹-7 817 O CH CH CH Ar¹⁸ R¹¹-8 818 O CH CH CH Ar¹⁸ R¹¹-9 819 O CH CH CH Ar¹⁸ R¹¹-10 820 O CH CH CH Ar¹⁸ R¹¹-11 821 O CH CH CH Ar¹⁸ R¹¹-12 822 O CH CH CH Ar¹⁸ R¹¹-13 823 O CH CH CH Ar¹⁸ R¹¹-14 824 O CH CH CH Ar¹⁸ R¹¹-15 825 O CH CH CH Ar¹⁸ R¹¹-16 826 O CH CH CH Ar¹⁸ R¹¹-17 827 O CH CH CH Ar¹⁸ R¹¹-18 828 O CH CH CH Ar¹⁸ R¹¹-19 829 O CH CH CH Ar¹⁸ R¹¹-20 830 O CH CH CH Ar¹⁸ R¹¹-21 831 O CH CH CH Ar¹⁸ R¹¹-22 832 O CH CH CH Ar¹⁸ R¹¹-23 833 O CH CH CH Ar¹⁸ R¹¹-25 834 O CH CH CH Ar¹⁸ R¹¹-26 835 O CH CH CH Ar¹⁸ R¹¹-27 836 O CH CH CH Ar¹⁸ R¹¹-28 837 O CH CH CH Ar¹⁸ R¹¹-29 838 O CH CH CH Ar¹⁸ A¹¹-1 839 O CH CH CH Ar¹⁸ A¹¹-2 840 O CH CH CH Ar¹⁸ A¹¹-3 841 S CH CH CH Ar¹ R¹¹-1 842 S CH CH CH Ar¹ R¹¹-2 843 S CH CH CH Ar¹ R¹¹-3 844 S CH CH CH Ar¹ R¹¹-5 845 S CH CH CH Ar¹ R¹¹-6 846 S CH CH CH Ar¹ R¹¹-7 847 S CH CH CH Ar¹ R¹¹-8 848 S CH CH CH Ar¹ R¹¹-9 849 S CH CH CH Ar¹ R¹¹-10 850 S CH CH CH Ar¹ R¹¹-11 851 S CH CH CH Ar¹ R¹¹-12 852 S CH CH CH Ar¹ R¹¹-13 853 S CH CH CH Ar¹ R¹¹-14 854 S CH CH CH Ar¹ R¹¹-15 855 S CH CH CH Ar¹ R¹¹-16 856 S CH CH CH Ar¹ R¹¹-17 857 S CH CH CH Ar¹ R¹¹-18 858 S CH CH CH Ar¹ R¹¹-19 859 S CH CH CH Ar¹ R¹¹-20 860 S CH CH CH Ar¹ R¹¹-21 861 S CH CH CH Ar¹ R¹¹-22 862 S CH CH CH Ar¹ R¹¹-23 863 S CH CH CH Ar¹ R¹¹-25 864 S CH CH CH Ar¹ R¹¹-26 865 S CH CH CH Ar¹ R¹¹-27 866 S CH CH CH Ar¹ R¹¹-28 867 S CH CH CH Ar¹ R¹¹-29 868 S CH CH CH Ar¹ A¹¹-1 869 S CH CH CH Ar¹ A¹¹-2 870 S CH CH CH Ar¹ A¹¹-3 871 S CH CH CH Ar² R¹¹-1 872 S CH CH CH Ar² R¹¹-2 873 S CH CH CH Ar² R¹¹-3 874 S CH CH CH Ar² R¹¹-5 875 S CH CH CH Ar² R¹¹-6 876 S CH CH CH Ar² R¹¹-7 877 S CH CH CH Ar² R¹¹-8 878 S CH CH CH Ar² R¹¹-9 879 S CH CH CH Ar² R¹¹-10 880 S CH CH CH Ar² R¹¹-11 881 S CH CH CH Ar² R¹¹-12 882 S CH CH CH Ar² R¹¹-13 883 S CH CH CH Ar² R¹¹-14 884 S CH CH CH Ar² R¹¹-15 885 S CH CH CH Ar² R¹¹-16 886 S CH CH CH Ar² R¹¹-17 887 S CH CH CH Ar² R¹¹-18 888 S CH CH CH Ar² R¹¹-19 889 S CH CH CH Ar² R¹¹-20 890 S CH CH CH Ar² R¹¹-21 891 S CH CH CH Ar² R¹¹-22 892 S CH CH CH Ar² R¹¹-23 893 S CH CH CH Ar² R¹¹-25 894 S CH CH CH Ar² R¹¹-26 895 S CH CH CH Ar² R¹¹-27 896 S CH CH CH Ar² R¹¹-28 897 S CH CH CH Ar² R¹¹-29 898 S CH CH CH Ar² A¹¹-1 899 S CH CH CH Ar² A¹¹-2 900 S CH CH CH Ar² A¹¹-3 901 S CH CH CH Ar³ R¹¹-1 902 S CH CH CH Ar³ R¹¹-2 903 S CH CH CH Ar³ R¹¹-3 904 S CH CH CH Ar³ R¹¹-5 905 S CH CH CH Ar³ R¹¹-6 906 S CH CH CH Ar³ R¹¹-7 907 S CH CH CH Ar³ R¹¹-8 908 S CH CH CH Ar³ R¹¹-9 909 S CH CH CH Ar³ R¹¹-10 910 S CH CH CH Ar³ R¹¹-11 911 S CH CH CH Ar³ R¹¹-12 912 S CH CH CH Ar³ R¹¹-13 913 S CH CH CH Ar³ R¹¹-14 914 S CH CH CH Ar³ R¹¹-15 915 S CH CH CH Ar³ R¹¹-16 916 S CH CH CH Ar³ R¹¹-17 917 S CH CH CH Ar³ R¹¹-18 918 S CH CH CH Ar³ R¹¹-19 919 S CH CH CH Ar³ R¹¹-20 920 S CH CH CH Ar³ R¹¹-21 921 S CH CH CH Ar³ R¹¹-22 922 S CH CH CH Ar³ R¹¹-23 923 S CH CH CH Ar³ R¹¹-25 924 S CH CH CH Ar³ R¹¹-26 925 S CH CH CH Ar³ R¹¹-27 926 S CH CH CH Ar³ R¹¹-28 927 S CH CH CH Ar³ R¹¹-29 928 S CH CH CH Ar³ A¹¹-1 929 S CH CH CH Ar³ A¹¹-2 930 S CH CH CH Ar³ A¹¹-3 931 S CH CH CH Ar⁴ R¹¹-1 932 S CH CH CH Ar⁴ R¹¹-2 933 S CH CH CH Ar⁴ R¹¹-3 934 S CH CH CH Ar⁴ R¹¹-5 935 S CH CH CH Ar⁴ R¹¹-6 936 S CH CH CH Ar⁴ R¹¹-7 937 S CH CH CH Ar⁴ R¹¹-8 938 S CH CH CH Ar⁴ R¹¹-9 939 S CH CH CH Ar⁴ R¹¹-10 940 S CH CH CH Ar⁴ R¹¹-11 941 S CH CH CH Ar⁴ R¹¹-12 942 S CH CH CH Ar⁴ R¹¹-13 943 S CH CH CH Ar⁴ R¹¹-14 944 S CH CH CH Ar⁴ R¹¹-15 945 S CH CH CH Ar⁴ R¹¹-16 946 S CH CH CH Ar⁴ R¹¹-17 947 S CH CH CH Ar⁴ R¹¹-18 948 S CH CH CH Ar⁴ R¹¹-19 949 S CH CH CH Ar⁴ R¹¹-20 950 S CH CH CH Ar⁴ R¹¹-21 951 S CH CH CH Ar⁴ R¹¹-22 952 S CH CH CH Ar⁴ R¹¹-23 953 S CH CH CH Ar⁴ R¹¹-25 954 S CH CH CH Ar⁴ R¹¹-26 955 S CH CH CH Ar⁴ R¹¹-27 956 S CH CH CH Ar⁴ R¹¹-28 957 S CH CH CH Ar⁴ R¹¹-29 958 S CH CH CH Ar⁴ A¹¹-1 959 S CH CH CH Ar⁴ A¹¹-2 960 S CH CH CH Ar⁴ A¹¹-3 961 S CH CH CH Ar¹⁰ R¹¹-1 962 S CH CH CH Ar¹⁰ R¹¹-2 963 S CH CH CH Ar¹⁰ R¹¹-3 964 S CH CH CH Ar¹⁰ R¹¹-5 965 S CH CH CH Ar¹⁰ R¹¹-6 966 S CH CH CH Ar¹⁰ R¹¹-7 967 S CH CH CH Ar¹⁰ R¹¹-8 968 S CH CH CH Ar¹⁰ R¹¹-9 969 S CH CH CH Ar¹⁰ R¹¹-10 970 S CH CH CH Ar¹⁰ R¹¹-11 971 S CH CH CH Ar¹⁰ R¹¹-12 972 S CH CH CH Ar¹⁰ R¹¹-13 973 S CH CH CH Ar¹⁰ R¹¹-14 974 S CH CH CH Ar¹⁰ R¹¹-15 975 S CH CH CH Ar¹⁰ R¹¹-16 976 S CH CH CH Ar¹⁰ R¹¹-17 977 S CH CH CH Ar¹⁰ R¹¹-18 978 S CH CH CH Ar¹⁰ R¹¹-19 979 S CH CH CH Ar¹⁰ R¹¹-20 980 S CH CH CH Ar¹⁰ R¹¹-21 981 S CH CH CH Ar¹⁰ R¹¹-22 982 S CH CH CH Ar¹⁰ R¹¹-23 983 S CH CH CH Ar¹⁰ R¹¹-25 984 S CH CH CH Ar¹⁰ R¹¹-26 985 S CH CH CH Ar¹⁰ R¹¹-27 986 S CH CH CH Ar¹⁰ R¹¹-28 987 S CH CH CH Ar¹⁰ R¹¹-29 988 S CH CH CH Ar¹⁰ A¹¹-1 989 S CH CH CH Ar¹⁰ A¹¹-2 990 S CH CH CH Ar¹⁰ A¹¹-3 991 S CH CH CH Ar¹⁷ R¹¹-1 992 S CH CH CH Ar¹⁷ R¹¹-2 993 S CH CH CH Ar¹⁷ R¹¹-3 994 S CH CH CH Ar¹⁷ R¹¹-5 995 S CH CH CH Ar¹⁷ R¹¹-6 996 S CH CH CH Ar¹⁷ R¹¹-7 997 S CH CH CH Ar¹⁷ R¹¹-8 998 S CH CH CH Ar¹⁷ R¹¹-9 999 S CH CH CH Ar¹⁷ R¹¹-10 1000 S CH CH CH Ar¹⁷ R¹¹-11 1001 S CH CH CH Ar¹⁷ R¹¹-12 1002 S CH CH CH Ar¹⁷ R¹¹-13 1003 S CH CH CH Ar¹⁷ R¹¹-14 1004 S CH CH CH Ar¹⁷ R¹¹-15 1005 S CH CH CH Ar¹⁷ R¹¹-16 1006 S CH CH CH Ar¹⁷ R¹¹-17 1007 S CH CH CH Ar¹⁷ R¹¹-18 1008 S CH CH CH Ar¹⁷ R¹¹-19 1009 S CH CH CH Ar¹⁷ R¹¹-20 1010 S CH CH CH Ar¹⁷ R¹¹-21 1011 S CH CH CH Ar¹⁷ R¹¹-22 1012 S CH CH CH Ar¹⁷ R¹¹-23 1013 S CH CH CH Ar¹⁷ R¹¹-25 1014 S CH CH CH Ar¹⁷ R¹¹-26 1015 S CH CH CH Ar¹⁷ R¹¹-27 1016 S CH CH CH Ar¹⁷ R¹¹-28 1017 S CH CH CH Ar¹⁷ R¹¹-29 1018 S CH CH CH Ar¹⁷ A¹¹-1 1019 S CH CH CH Ar¹⁷ A¹¹-2 1020 S CH CH CH Ar¹⁷ A¹¹-3 1021 S CH CH CH Ar¹⁸ R¹¹-1 1022 S CH CH CH Ar¹⁸ R¹¹-2 1023 S CH CH CH Ar¹⁸ R¹¹-3 1024 S CH CH CH Ar¹⁸ R¹¹-5 1025 S CH CH CH Ar¹⁸ R¹¹-6 1026 S CH CH CH Ar¹⁸ R¹¹-7 1027 S CH CH CH Ar¹⁸ R¹¹-8 1028 S CH CH CH Ar¹⁸ R¹¹-9 1029 S CH CH CH Ar¹⁸ R¹¹-10 1030 S CH CH CH Ar¹⁸ R¹¹-11 1031 S CH CH CH Ar¹⁸ R¹¹-12 1032 S CH CH CH Ar¹⁸ R¹¹-13 1033 S CH CH CH Ar¹⁸ R¹¹-14 1034 S CH CH CH Ar¹⁸ R¹¹-15 1035 S CH CH CH Ar¹⁸ R¹¹-16 1036 S CH CH CH Ar¹⁸ R¹¹-17 1037 S CH CH CH Ar¹⁸ R¹¹-18 1038 S CH CH CH Ar¹⁸ R¹¹-19 1039 S CH CH CH Ar¹⁸ R¹¹-20 1040 S CH CH CH Ar¹⁸ R¹¹-21 1041 S CH CH CH Ar¹⁸ R¹¹-22 1042 S CH CH CH Ar¹⁸ R¹¹-23 1043 S CH CH CH Ar¹⁸ R¹¹-25 1044 S CH CH CH Ar¹⁸ R¹¹-26 1045 S CH CH CH Ar¹⁸ R¹¹-27 1046 S CH CH CH Ar¹⁸ R¹¹-28 1047 S CH CH CH Ar¹⁸ R¹¹-29 1048 S CH CH CH Ar¹⁸ A¹¹-1 1049 S CH CH CH Ar¹⁸ A¹¹-2 1050 S CH CH CH Ar¹⁸ A¹¹-3

As used herein, the term “compound(s) of the present invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to as “compound(s) of formula I” or “compound(s) I” or “formula I compound(s)”, and includes their salts, tautomers, stereoisomers, and N-oxides.

The present invention also relates to a mixture of at least one compound of the invention with at least one mixing partner as defined herein. Preferred are binary mixtures of one compound of the invention as component I with one mixing partner as defined herein as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1:5000, preferably from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, particularly from 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.

Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers. Preferred mixing partners are insecticides, nematicides and fungicides.

The following list M of pesticides, grouped and numbered according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:

M.1 Acetylcholine esterase (AChE) inhibitors: M.1A carbamates, e.g. aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathionmethyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin,metofluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.1 4,5-Dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine, M.4A.2: (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflumezopyrim;

M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spinetoram;

M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues hydroprene, kinoprene, and methoprene; or M.76 fenoxycarb, or M.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.86 chloropicrin, M.8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic;

M.9 Chordotonal organ TRPV channel modulators, e.g. M.96 pymetrozine; pyrifluquinazon;

M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;

M.11 Microbial disruptors of insect midgut membranes, e.g. Bacillus thuringiensis or Bacillus sphaericus and the insecticdal proteins they produce such as Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai Bacillus thuringiensis subsp. kurstakiand Bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1;

M.12 Inhibitors of mitochondrial ATP synthase, e.g. M.12A diafenthiuron, or M.12B organotin miticides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetradifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g. chlorfenapyr, DNOC, or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, e.g. nereistoxin analogues bensultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1, e.g. buprofezin;

M.17 Moulting disruptors, Dipteran, e.g. cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;

M.19 Octopamin receptor agonists, e.g. amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, e.g. M.20A hydramethylnon,

M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;

M.21 Mitochondrial complex I electron transport inhibitors, e.g. M.21A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;

M.22 Voltage-dependent sodium channel blockers, e.g. M.22A indoxacarb, M.22B metaflumizone, or M.22B.1: 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4-chloro-phenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;

M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion;

M.24 Mitochondrial complex IV electron transport inhibitors, e.g. M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlorantraniliprole, cyantraniliprole, tetraniliprole, M.28.1: (R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetra-fluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid, M.28.2: (S)-3-Chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5c) N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5i) N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethypamino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide; M.28.5l) N-[4-Chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methyl-phenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide; or

M.29: Chordotonal organ Modulators—undefined target site, e.g. flonicamid;

M.UN. insecticidal active compounds of unknown or uncertain mode of action, e.g. afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metaldehyde, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, M.UN.3: 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-aza-dispiro[4.2.4.2]-tetradec-11-en-10-one,

M.UN.4: 3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,

M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine, or actives on basis of Bacillus firmus (Votivo, I-1582);

M.UN.6: flupyrimin;

M.UN.8: fluazaindolizine; M.UN.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; M.UN.9.b): fluxametamide; M.UN.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;

M.UN.11.i) 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11.j) 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.l) N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethypethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.m) N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11.o) 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethypethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11.p) N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluorome-thyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or

M.UN.12.a) 2-(1,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.UN.12.b) 2-[6-[2-(5-Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.c) 2-[6-[2-(3-Pyridinyl)-5-thia-zolyl]-2-pyridinyl]-pyrimidine; M.UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.UN.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;

M.UN.14a) 1-[(6-Chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; or M.UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol;

M.UN.16a) 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.UN.16b) 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16c) N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide; M.UN.16d) 1-[1-(1-cyanocyclopropypethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16e) N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16f) 1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16g) 1-[1-(1-cyanocyclopropypethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16h) N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16i) 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.UN.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide,

M.UN.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.UN.17b) N-cyclo-propyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.UN.17c) N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; M.UN.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; M.UN.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.UN.171) 2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyra-zinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,

M.UN.18. tyclopyrazoflor;

M.UN.19 sarolaner, M.UN.20 lotilaner;

M.U N.21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; M.UN.22a 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethypimidazo[4,5-b]pyridine, or M.UN.22b 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethypimidazo[4,5-b]pyridine;

M.UN.23a) 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide, or M.UN.23b) 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide;

M.UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; M.UN.25 acynonapyr; M.UN.26 benzpyrimoxan; M.UN.27 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide; M.UN.28 Oxazosulfyl;

M.UN.29a) [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; M.UN.29b) [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; M.UN.29c) [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; M.UN.29d) [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; M.UN.29.e) (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one or M.UN.29f) (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one.

The commercially available compounds of the group M listed above may be found in The Pesticide Manual, 17th Edition, C. MacBean, British Crop Protection Council (2015) among other publications. The online Pesticide Manual is updated regularly and is accessible through http://bcpcdata.com/pesticide-manual.html.

Another online data base for pesticides providing the ISO common names is http://www.alanwood.net/pesticides.

The M.4 cycloxaprid is known from WO2010/069266 and WO2011/069456. M.4A.1 is known from CN 103814937; CN105367557, CN 105481839. M.4A.2, guadipyr, is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO 2007/101369. M.22B.1 is described in CN10171577 and M.22B.2 in CN102126994. Spiropidion M.23.1 is known from WO 2014/191271. M.28.1 and M.28.2 are known from WO2007/101540. M.28.3 is described in WO2005/077934. M.28.4 is described in WO2007/043677. M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO 2013/024010, M.28.5i) is described in WO2011/085575, M.28.5j) in WO2008/134969, M.28.5k) in US2011/046186 and M.28.51) in WO2012/034403. M.28.6 can be found in WO2012/034472. M.UN.3 is known from WO2006/089633 and M.UN.4 from WO2008/067911. M.UN.5 is described in WO2006/043635, and biological control agents on the basis of Bacillus firmus are described in WO2009/124707. Flupyrimin is described in WO2012/029672. M.UN.8 is known from WO2013/055584. M.UN.9.a) is described in WO2013/050317. M.UN.9.b) is described in WO2014/126208. M.UN.10 is known from WO2010/060379. Broflanilide and M.UN.11.b) to M.UN.11.h) are described in WO2010/018714, and M.UN.11i) to M.UN.11.p) in WO 2010/127926. M.UN.12.a) to M.UN.12.c) are known from WO2010/006713, M.UN.12.d) and M.UN.12.e) are known from WO2012/000896. M.UN.14a) and M.UN.14b) are known from WO2007/101369. M.UN.16.a) to M.UN.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497. M.UN.17a) to M.UN.17.j) are described in WO2015/038503. M.UN.18 Tyclo-prazoflor is described in US2014/0213448. M.UN.19 is described in WO2014/036056. M.UN.20 is known from WO2014/090918. M.UN.21 is known from EP2910126. M.UN.22a and M.UN.22b are known from WO2015/059039 and WO2015/190316. M.UN.23a and M.UN.23b are known from WO2013/050302. M.UN.24a) and M.UN.24b) are known from WO2012/126766. Acynonapyr M.UN.25 is known from WO 2011/105506. Benzpyrimoxan M.UN.26 is known from WO2016/104516. M.UN.27 is known from WO2016/174049. M.UN.28 Oxazosulfyl is known from WO2017/104592. M.UN.29a) to M.UN.29f) are known from WO2009/102736 or WO2013116053.

The following list of fungicides, in conjunction with which the compounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them:

A) Respiration Inhibitors

-   -   Inhibitors of complex III at Q_(o) site: azoxystrobin (A.1.1),         coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin         (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6),         fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8),         kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin         (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13),         pyraclostrobin (A.1.14), pyrametostrobin (A.1.15),         pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17),         2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide         (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb         (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21),         methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phe-nyl]-N-methoxy-carbamate         (A.1.22),         1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methylphenyl]-4-methyl-tetrazol-5-one         (A.1.25),         (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide         (A.1.34),         (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide         (A.1.35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37),         2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic         acid methylester (A.1.38);     -   inhibitors of complex III at Q_(i) site: cyazofamid (A.2.1),         amisulbrom (A.2.2),         [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]         2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4);     -   inhibitors of complex II: benodanil (A.3.1), benzovindiflupyr         (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5),         fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8),         fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.11),         isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14),         penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen         (A.3.17), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam         (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22),         pyrapropoyne (A.3.23), fluindapyr (A.3.28), methyl         (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate         (A.3.30), isoflucypram (A.3.31),         2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-Apyridine-3-carboxamide         (A.3.32),         2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide         (A.3.33),         2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide         (A.3.34),         2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide         (A.3.35),         2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide         (A.3.36),         2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide         (A.3.37),         2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide         (A.3.38),         2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide         (A.3.39);     -   other respiration inhibitors: diflumetorim (A.4.1); nitrophenyl         derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap         (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone         (A.4.7); organometal compounds: fentin salts, e.g.         fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin         hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12);

B) Sterol Biosynthesis Inhibitors (SBI Fungicides)

-   -   C14 demethylase inhibitors: triazoles: azaconazole (B.1.1),         bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole         (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6),         diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole         (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11),         flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole         (B.1.14), ipconazole (B.1.15), metconazole (B.1.17),         myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole         (B.1.20), penconazole (B.1.21), propiconazole (B.1.22),         prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole         (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27),         triadimenol (B.1.28), triticonazole (B.1.29), uniconazole         (B.1.30),         2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol         (B.1.31),         2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol         (B.1.32), ipfentrifluconazole (B.1.37), mefentrifluconazole         (B.1.38),         2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol         (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45),         prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines,         pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50),         triforine (B.1.51),         [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol         (B.1.52);     -   Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph         (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4),         tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7),         spiroxamine (B.2.8);     -   Inhibitors of 3-keto reductase: fenhexamid (B.3.1);     -   Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1);

C) Nucleic Acid Synthesis Inhibitors

-   -   phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1),         benalaxyl-M (C.1.2), kiral-axyl (C.1.3), metalaxyl (C.1.4),         metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);     -   other nucleic acid synthesis inhibitors: hymexazole (C.2.1),         octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4),         5-fluorocytosine (C.2.5),         5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6),         5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7),         5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);

D) Inhibitors of Cell Division and Cytoskeleton

-   -   tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2),         fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl         (D.1.5),         3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine         (D.1.6),         3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine         (D.1.7),         N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide         (D.1.8),         N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide         (D.1.9),         2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide         (D.1.10),         2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide         (D.1.11),         2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide         (D.1.12),         2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide         (D.1.13),         2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide         (D.1.14),         2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide         (D.1.15),         4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine         (D.1.16);     -   other cell division inhibitors: diethofencarb (D.2.1), ethaboxam         (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide         (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);

E) Inhibitors of Amino Acid and Protein Synthesis

-   -   methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim         (E.1.2), pyrimethanil (E.1.3);     -   protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin         (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin         (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);

F) Signal Transduction Inhibitors

-   -   MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione         (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil         (F.1.5);     -   G protein inhibitors: quinoxyfen (F.2.1);

G) Lipid and Membrane Synthesis Inhibitors

-   -   Phospholipid biosynthesis inhibitors: edifenphos (G.1.1),         iprobenfos (G.1.2), pyrazophos

(G.1.3), isoprothiolane (G.1.4);

-   -   lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2),         tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5),         chloroneb (G.2.6), etridiazole (G.2.7);     -   phospholipid biosynthesis and cell wall deposition: dimethomorph         (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph         (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6),         valifenalate (G.3.7);     -   compounds affecting cell membrane permeability and fatty acides:         propamocarb (G.4.1);     -   inhibitors of oxysterol binding protein: oxathiapiprolin         (G.5.1),         2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl         methanesulfonate (G.5.2),         2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)         1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl         methanesulfonate (G.5.3),         4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide         (G.5.4),         4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide         (G.5.5),         4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide         (G.5.6),         4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide         (G.5.7),         4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide         (G.5.8),         4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide         (G.5.9),         4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide         (G.5.10),         (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide         (G.5.11);

H) Inhibitors with Multi Site Action

-   -   inorganic active substances: Bordeaux mixture (H.1.1), copper         (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4),         copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur         (H.1.7);     -   thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2),         maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6),         thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);     -   organochlorine compounds: anilazine (H.3.1), chlorothalonil         (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5),         dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene         (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide         (H.3.10), tolylfluanid (H.3.11);     -   guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine         free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5),         iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7),         iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9),         2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone         (H.4.10);

I) Cell Wall Synthesis Inhibitors

-   -   inhibitors of glucan synthesis: validamycin (I.1.1), polyoxin B         (I.1.2);     -   melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole         (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil         (I.2.5);

J) Plant Defence Inducers

-   -   acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil         (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5);         phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7),         phosphorous acid and its salts (J.1.8), calcium phosphonate         (J.1.11), potassium phosphonate (J.1.12), potassium or sodium         bicarbonate (J.1.9),         4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide         (J 1.10);

K) Unknown Mode of Action

-   -   bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3),         cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocymet         (K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9),         difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11),         fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover         (K.1.14), flusulfamide (K.1.15), flutianil (K.1.16), harpin         (K.1.17), methasulfocarb (K.1.18), nitrapyrin (K.1.19),         nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), oxin-copper         (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24),         tecloftalam (K.1.25), triazoxide (K.1.26),         N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl         formamidine (K.1.27),         N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl         formamidine (K.1.28),         N′-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine         (K.1.29),         N′-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine         (K.1.30),         N′-[5-bromo-6-[1-(3,5-difluorophenypethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine         (K.1.31),         N′-[5-bromo-6-(4-isopropylcyclo-hexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine         (K.1.32),         N′-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine         (K.1.33),         N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl         formamidine (K.1.34),         N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl         formamidine (K.1.35),         2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide         (K.1.36),         3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine         (pyrisoxazole) (K.1.37),         3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine         (K.1.38),         5-chloro-1-(4,6-di-methoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole         (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate         (K.1.40), picarbutrazox (K.1.41), pentyl         N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate         (K.1.42), but-3-ynyl         N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate         (K.1.43),         2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol         (K.1.44),         2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol         (K.1.45), quinofumelin (K.1.47),         9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine         (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50),         2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline         (K.1.51), dichlobentiazox (K.1.52),         N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine         (K.1.53), pyrifenamine (K.1.54).

The fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.

The active substances mentioned above, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; U.S. Pat. Nos. 3,296,272; 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271, WO 11/028657, WO 12/168188, WO 07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO 13/092224, WO 11/135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/116251, WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511, WO 11/081174, WO 13/47441). Some compounds are identified by their CAS Registry Number which is separated by hyphens into three parts, the first consisting from two up to seven digits, the second consisting of two digits, and the third consisting of a single digit.

Suitable mixing partners for the compounds of the present invention also include biopesticides.

Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides fall into two major classes, microbial and biochemical pesticides:

(1) Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.

(2) Biochemical pesticides are naturally occurring substances or or structurally-similar and functionally identical to a naturally-occurring substance and extracts from biological sources that control pests or provide other crop protection uses as defined below, but have non-toxic mode of actions (such as growth or developmental regulation, attractents, repellents or defence activators (e.g. induced resistance) and are relatively non-toxic to mammals.

Biopesticides for use against crop diseases have already established themselves on a variety of crops. For example, biopesticides already play an important role in controlling downy mildew diseases. Their benefits include: a 0-Day Pre-Harvest Interval, the ability to use under moderate to severe disease pressure, and the ability to use in mixture or in a rotational program with other registered pesticides.

A major growth area for biopesticides is in the area of seed treatments and soil amendments. Biopesticidal seed treatments are e.g. used to control soil borne fungal pathogens that cause seed rots, damping-off, root rot and seedling blights. They can also be used to control internal seed borne fungal pathogens as well as fungal pathogens that are on the surface of the seed. Many biopesticidal products also show capacities to stimulate plant host defenses and other physiological processes that can make treated crops more resistant to a variety of biotic and abiotic stresses or can regulate plant growth. Many biopesticidal products also show capacities to stimulate plant health, plant growth and/or yield enhancing activity.

The following list of biopesticides, in conjunction with which the compounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them:

L) Biopesticides

L1) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also named Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibaclllus alvei, Paenibaclllus epiphyticus, P. polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, zucchini yellow mosaic virus (avirulent strain);

L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein, Reynoutria sachalinensis extract;

L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beauveria bassiana, B. brongniartll, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popillae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus;

L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl 1-butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, pentatermanone, (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (2)-11-tetradecenal, (Z)-11-tetradecen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropici, Sinorhizobium meliloti.

The biopesticides from group L1) and/or L2) may also have insecticidal, acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity. The biopesticides from group L3) and/or L4) may also have fungicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity. The biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity.

Many of these biopesticides have been deposited under deposition numbers mentioned herein (the prefices such as ATCC or DSM refer to the acronym of the respective culture collection, for details see e.g. here: http://www.wfcc.info/ccinfo/collection/by_acronym/), are referred to in literature, registered and/or are commercially available: mixtures of Aureobasidium pullulans DSM 14940 and DSM 14941 isolated in 1989 in Konstanz, Germany (e.g. blastospores in BlossomProtect® from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 originally isolated in wheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR 11005; e.g. GELFIX® Gramineas from BASF Agricultural Specialties Ltd., Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e.g. in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Maiz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; U.S. Pat. No. 8,445,255); B. amyloliquefaciens spp. plantarum D747 isolated from air in Kikugawa-shi, Japan (US 20130236522 A1; FERM BP-8234; e.g. Double Nickel™ 55 WDG from Certis LLC, USA), B. amyloliquefaciens spp. plantarum FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. Taegro® from Novozyme Biologicals, Inc., USA), B. amyloliquefaciens ssp. plantarum FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. amyloliquefaciens ssp. plantarum MBI600 isolated from faba bean in Sutton Bonington, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B-50595; US 2012/0149571 A1; e.g. Integral® from BASF Corp., USA), B. amyloliquefaciens spp. plantarum QST-713 isolated from peach orchard in 1995 in California, U.S.A. (NRRL B-21661; e.g. Serenade® MAX from Bayer Crop Science LP, USA), B. amyloliquefaciens spp. plantarum TJ1000 isolated in 1992 in South Dakota, U.S.A. (also called 1BE; ATCC BAA-390; CA 2471555 A1; e.g. QuickRoots™ from TJ Technologies, Watertown, S. Dak., USA), B. firmus CNCM I-1582, a variant of parental strain EIP-N1 (CNCM I-1556) isolated from soil of central plain area of Israel (WO 2009/126473, U.S. Pat. No. 6,406,690; e.g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizosphere in Mexico (IDAC 260707-01; e.g. PROMIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to as BU-F22 and BU-F33 isolated at least before 1993 from cucumber infested by Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; U.S. Pat. No. 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014/029697; e.g. BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B-30087; e.g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; U.S. Pat. No. 8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US 2010/0260735; WO 2011/109395); B. thuringiensis ssp. aizawai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wis., U.S.A., in 1987 (also called ABG-6346; ATCC SD-1372; e.g. XenTari® from BioFa AG, Münsingen, Germany), B. t. ssp. kurstaki ABTS-351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Tex., U.S.A. (ATCC SD-1275; e.g. Dipel® DF from Valent BioSciences, Ill., USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B-50753; e.g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1, a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585 215 B1; e.g. Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g. Broad Band® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g. in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); B. japonicum strains deposited at SEMIA known from Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in Cerrados region, Brazil by Embrapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under lab conditions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, being a natural variant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO 2013/032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitans CON/M/91-08 isolated from oilseed rape (WO 1996/021358; DSM 9660; e.g. Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g. Messenger™ or HARP-N-Tek from Plant Health Care plc, U.K.), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; e.g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (e.g. Gemstar® from Certis LLC, USA), Helicoverpa zea nucleopolyhedrovirus ABA-NPV-U (e.g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e.g. Nemasys® G from BASF Agricultural Specialities Limited, UK), Isaria fumosorosea Apopka-97 isolated from mealy bug on gynura in Apopka, Fla., U.S.A. (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e.g. PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhizium anisopliae var. anisopliae F52 also called 275 or V275 isolated from codling moth in Austria (DSM 3884, ATCC 90448; e.g. Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in the central part of Israel (U.S. Pat. No. 6,994,849; NRRL Y-30752; e.g. formerly Shemer® from Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89/030550; WO1991/02051; Crop Protection 27, 352-361, 2008; e.g. BioAct®from Bayer CropScience AG, Germany and MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014/029697; NRRL B-50755; e.g. BAC-UP from BASF Agricultural Specialties (Pty) Ltd., South Africa), Paenibacillus strains isolated from soil samples from a variety of European locations including Germany: P. epiphyticus Lu17015 (WO 2016/020371; DSM 26971), P. polymyxa ssp. plantarum Lu16774 (WO 2016/020371; DSM 26969), P. p. ssp. plantarum strain Lu17007 (WO 2016/020371; DSM 26970); Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000s in Illinois, U.S.A. (ATCC SD-5833; Federal Register 76(22), 5808, Feb. 2, 2011; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA), Penicillium bilaiae (also called P. bilail) strains ATCC 18309 (=ATCC 74319), ATCC 20851 and/or ATCC 22348 (=ATCC 74318) originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102, 1998; U.S. Pat. No. 5,026,417, WO 1995/017806; e.g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (EP 0307510 B1; e.g. Regalia® SC from Marrone BioInovations, Davis, Calif., USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae (e.g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK), Streptomyces microflavus NRRL B-50550 (WO 2014/124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41R isolated in South Africa (NRRL 50759; also referred to as T. fertile; e.g. Trichoplus® from BASF Agricultural Specialities (Pty) Ltd., South Africa), T. harzianum T-22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e.g. Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Wert, Ohio, USA).

According to the invention, the solid material (dry matter) of the biopesticides (with the exception of oils such as Neem oil) are considered as active components (e.g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).

In accordance with the present invention, the weight ratios and percentages used herein for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).

The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of CFU of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1×10¹⁰ CFU equals one gram of total weight of the respective active component. Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells. In addition, here “CFU” may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, such as Steinernema feltiae.

When mixtures comprising microbial pesticides are employed in crop protection, the application rates preferably range from about 1×10⁶ to 5×10¹⁵ (or more) CFU/ha, preferably from about 1×10⁸ to about 1×10¹³ CFU/ha, and even more preferably from about 1×10⁹ to about 1×10¹² CFU/ha. In the case of (entomopathogenic) nematodes as microbial pesticides (e.g. Steinernema feltiae), the application rates preferably range inform about 1×10⁵ to 1×10¹² (or more), more preferably from 1×10⁸ to 1×10¹¹, even more preferably from 5×10⁸ to 1×10¹⁰ individuals (e.g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.

When mixtures comprising microbial pesticides are employed in seed treatment, the application rates with respect to plant propagation material preferably range from about 1×10⁶ to 1×10¹² (or more) CFU/seed. Preferably, the concentration is about 1×10⁶ to about 1×10⁹ CFU/seed. In the case of the microbial pesticides II, the application rates with respect to plant propagation material also preferably range from about 1×10⁷ to 1×10¹⁴ (or more) CFU per 100 kg of seed, preferably from 1×10⁹ to about 1×10¹² CFU per 100 kg of seed.

The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.

An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof. The term “pesticidally effective amount” is defined below.

The compounds of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.)

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl-sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer-rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

-   -   i) Water-soluble concentrates (SL, LS)

10-60 wt % of a compound I according to the invention and 5-15 wt % wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt %. The active substance dissolves upon dilution with water.

-   -   ii) Dispersible concentrates (DC)

5-25 wt % of a compound I according to the invention and 1-10 wt % dispersant (e.g. polyvinylpyrrolidone) are dissolved in up to 100 wt % organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.

-   -   iii) Emulsifiable concentrates (EC)

15-70 wt % of a compound I according to the invention and 5-10 wt % emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt % water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.

-   -   iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I according to the invention and 1-10 wt % emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt % water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

-   -   v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I according to the invention are comminuted with addition of 2-10 wt % dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0, 1-2 wt % thickener (e.g. xanthan gum) and up to 100 wt % water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt % binder (e.g. polyvinylalcohol) is added.

-   -   vi) Water-dispersible granules and water-soluble granules (WG,         SG)

50-80 wt % of a compound I according to the invention are ground finely with addition of up to 100 wt % dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

-   -   vii) Water-dispersible powders and water-soluble powders (WP,         SP, WS)

50-80 wt % of a compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodium lignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) and up to 100 wt % solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.

-   -   viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a compound I according to the invention are comminuted with addition of 3-10 wt % dispersants (e.g. sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose) and up to 100 wt % water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

-   -   ix) Microemulsion (ME)

5-20 wt % of a compound I according to the invention are added to 5-30 wt % organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt % surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water up to 100%. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

-   -   x) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I according to the invention, 0-40 wt % water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt % of a compound I according to the invention, 0-40 wt % water insolu-ble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4′-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the for-mation of a polyurea microcapsule. The monomers amount to 1-10 wt %. The wt % relate to the total CS composition.

-   -   xi) Dustable powders (DP, DS)

1-10 wt % of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt % solid carrier, e.g. finely divided kaolin.

-   -   xii) Granules (GR, FG)

0.5-30 wt % of a compound I according to the invention is ground finely and associated with up to 100 wt % solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.

-   -   xiii) Ultra-low volume liquids (UL)

1-50 wt % of a compound I according to the invention are dissolved in up to 100 wt % organic solvent, e.g. aromatic hydrocarbon.

The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds of the present invention and/or mixing partners as defined above, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds of the present invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.

The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the present invention.

The compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the present invention.

The compounds of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.

The compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above. The components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture “in situ” on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.

The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.

Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow. Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the present invention. Suitable pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.

As used herein, the term “contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).

The term “animal pest” includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.

The term “crop” refers to both, growing and harvested crops.

The term “plant” includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize/sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as beans, lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, pumpkins, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevie); natural rubber plants or ornamental and forestry plants, such as flowers (e.g. carnation, petunias, geranium/pelargoniums, pansies and impatiens), shrubs, broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.

The term “cultivated plants” is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.

Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.

Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. However, most of the herbicide tolerance traits have been created via the use of transgenes.

Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.

Transgenes which have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

Transgenic corn events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, VCO-Ø1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTØH2, W62, W98, FG72 and CV127.

Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec. and synthetic variants thereof, like cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particular genes coding for protease inhibitors, like CpTI and pinII. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7.

Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.

Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701, MON87751 and DAS-81419.

Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

Cultivated plants comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.

Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-ØØ41Ø-5.

Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.

Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. For example, detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations “International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “Center for Environmental Risk Assessment (CERA)” (http://cera-gmc.org/GMCropDatabase), Further information on specific events and methods to detect them can be found for canola events MS1, MS8, RF3, GT73, MON88302, KK179 in WO01/031042, WO01/041558, WO01/041558, WO02/036831, WO11/153186, WO13/003558, for cotton events MON1445, MON15985, MON531(MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, 81910 in WO02/034946, WO02/100163, WO02/100163, WO03/013224, WO04/072235, WO04/039986, WO05/103266, WO05/103266, WO06/128573, WO07/017186, WO08/122406, WO08/151780, WO12/134808, WO13/112527, for corn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, MON87419 in WO98/044140, US02/102582, US03/126634, WO04/099447, WO04/011601, WO05/103301, WO05/061720, WO05/059103, WO06/098952, WO06/039376, US2007/292854, WO07/142840, WO07/140256, WO08/112019, WO09/103049, WO09/111263, WO10/077816, WO11/084621, WO11/062904, WO11/022469, WO13/169923, WO14/116854, WO15/053998, WO15/142571, for potato events E12, F10, J3, J55, V11, X17, Y9 in WO14/178910, WO14/178913, WO14/178941, WO14/179276, WO16/183445, WO17/062831, WO17/062825, for rice events LLRICE06, LLRICE601, LLRICE62 in WO00/026345, WO00/026356, WO00/026345 for soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419×DA544406-6, MON87751 in WO04/074492, WO06/130436, WO06/108674, WO06/108675, WO08/054747, WO08/002872, WO09/064652, WO09/102873, WO10/080829, WO10/037016, WO11/066384, WO11/034704, WO12/051199, WO12/082548, WO13/016527, WO13/016516, WO14/201235.

The use of compositions according to the invention on cultivated plants may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.

It has surprisingly been found that the pesticidal activity of the compounds of the present invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.

The term “plant propagation material” refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

The term “seed” embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.

In general, “pesticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.

In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.

The compounds of the invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects. The invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermination with a compound of the invention. The protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.

The term “seed treatment” comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods. Preferably, the seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.

The invention also comprises seeds coated with or containing the active compound. The term “coated with and/or containing” generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.

Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

In addition, the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.

Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included.

The active substance concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40% by weight.

In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Especially preferred FS formulations of the compounds of the invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20% by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5% by weight of a wetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% by weight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% by weight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40% by weight, e.g. 1 to 40% by weight of a binder (sticker/adhesion agent), optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of a thickener, optionally from 0.1 to 2% of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1% by weight and a filler/vehicle up to 100% by weight.

In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.

The invention therefore also relates to seed comprising a compound of the invention, or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.

The compounds of the invention may also be used for improving the health of a plant. There-fore, the invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the invention.

As used herein “an effective and non-phytotoxic amount” means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.

The terms “plant” and “plant propagation material” are defined above.

“Plant health” is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves (“greening effect”), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).

The above identified indicators for the health condition of a plant may be interdependent and may result from each other. Each indicator is defined in the art and can be determined by methods known to a skilled person.

The compounds of the invention are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds of the invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied). Furthermore, drenching and rodding methods can be used.

As used herein, the term “non-crop insect pest” refers to pests, which are particularly relevant for non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitos, crickets, or cockroaches.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature (e.g. http://www.pherobase.com), and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound. Formulations of the compounds of the invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries such as emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.

The oil spray formulations differ from the aerosol recipes in that no propellants are used.

For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.

The compounds of the invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.

The compounds of the invention and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).

Customary application rates in the protection of materials are, for example, from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m² treated material, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.

The compounds of the the invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:

insects from the order of Lepidoptera, for example Achroia grisella, Acleris spp. such as A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amyelois transitella, Anacampsis sarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota senatoria, Antheraea pernyi, Anticarsia (=Thermesia) spp. such as A. gemmatalis; Apamea spp., Aproaerema modicella, Archips spp. such as A. argyrospila, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp. such as A. velutinana; Athetis mindara, Austroasca viridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C. podana; Cactoblastis cactorum, Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, Chilo spp. such as C. Indicus, C. sup pressalis, C. partellus; Choreutis pariana, Choristoneura spp. such as C. conflictana, C. fumiferana, C. longicellana, C. murinana, C. occidentalis, C. rosaceana; Chrysodeixis (=Pseudoplusia) spp. such as C. eriosoma, C. includens; Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Colias eurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Corcyra cephalonica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis, Cydia (=Carpocapsa) spp. such as C. pomonella, C. latiferreana; Dalaca noctuides, Datana integerrima, Dasychira pinicola, Dendrolimus spp. such as D. pini, D. spectabilis, D. sibiricus; Desmia funeralis, Diaphania spp. such as D. nitidalis, D. hyalinata; Diatraea grandiosella, Diatraea saccharalis, Dipthera festiva, Earias spp. such as E. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curialis, Elasmopalpus lignosellus, Eldana saccharina, Endopiza viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. such as E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliana, Erionota thrax, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp. such as F. subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. such as G. funebrana, G. molesta, G. inopinata; Halysidota spp., Harrisina americana, Hedylepta spp., Helicoverpa spp. such as H. armigera (=Heliothis armigera), H. zea (=Heliothis zea); Heliothis spp. such as H. assulta, H. subflexa, H. virescens; Hellula spp. such as H. undalis, H. rogatalis; Helocoverpa gelotopoeon, Hemileuca oliviae, Herpetogramma licarsisalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantna cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoria flavofasciata, Keiferia lycopersicella, Lambdina fiscellaria fiscellaria, Lambdina fiscellaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma salicis, Leucoptera spp. such as L. coffeella, L. scitella; Leuminivora lycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattia octo (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotis albicosta, Loxostege spp. such as L. sticticalis, L. cereralis; Lymantria spp. such as L. dispar, L. monacha; Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp. such as M. americanum, M. californicum, M. constrictum, M. neustria; Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulalis, Megalopyge lanata, Melanchra picta, Melanitis leda, Mocis spp. such as M. lapites, M. repanda; Mocis latipes, Monochroa fragariae, Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantalis, Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisa anastomosalis, Operophtera brumata, Orgyia pseudotsugata, Oria spp., Orthaga thyrisalis, Ostrinia spp. such as O. nubilalis; Oulema oryzae, Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris, Papilio cresphontes, Paramyelois transitella, Paranthrene regalis, Paysandisia archon, Pectinophora spp. such as P. gossypiella; Peridroma saucia, Perileucoptera spp., such as P. coffeella; Phalera bucephala, Phryganidia californica, Phthorimaea spp. such as P. operculella; Phyllocnistis citrella, Phyllonorycter spp. such as P. blancardella, P. crataegella, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P. idaeusalis, P. stultana; Platyptilia carduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp, Plutella maculipennis, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus lepigone, Pseudaletia spp. such as P. sequax, P. unipuncta; Pyrausta nubilalis, Rachiplusia nu, Richia albicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festaliella, Scirpophaga spp. such as S. incertulas, S. innotata; Scotia segetum, Sesamia spp. such as S. inferens, Seudyra subflava, Sitotroga ce realella, Sparganothis pilleriana, Spilonota lechnaspis, S. ocellana, Spodoptera (=Lamphygma) spp. such as S. cosmoides, S. eridania, S. exigua, S. frugiperda, S. latisfascia, S. littoralis, S. litura, S. omithogalli; Stigmella spp., Stomopteryx subsecivella, Strymon bazochii, Sylepta derogata, Synanthedon spp. such as S. exitiosa, Tecia solanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophlebia) leucotreta, Thaumetopoea pityocampa, Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tinea spp. such as T. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp. such as T. viridana; Trichophaga tapetzella, Trichoplusia spp. such as T. ni; Tuta (=Scrobipalpula) absoluta, Udea spp. such as U. rubigalis, U. rubigalis; Virachola spp., Yponomeuta padella, and Zeiraphera canadensis;

insects from the order of Coleoptera, for example Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anxius, A. planipennis, A. sinuatus; Agriotes spp. such as A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimallus solstitialis, Anisandrus dispar, Anisoplia austriaca, Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophora spp. such as A. glabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as A. linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistria floridensis, Callosobruchus chinensis, Cameraria ohridella, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as C. assimilis, C. napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. such as C. vespertinus; Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. such as C. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dactylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. un decimpunctata, D. speciosa, D. longicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis), Enaphalodes rufulus, Epilachna spp. such as E. varivestis, E. vigintioctomaculata; Epitrix spp. such as E. hirtipennis, E. similaris; Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Gnathocerus cornutus, Hellula undaks, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp. such as H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L. melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea, Limonius californicus, Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp. such as L. bruneus; Liogenys fuscus, Macrodactylus spp. such as M. subspinosus; Maladera matrida, Megaplatypus mutates, Megascelis spp., Melanotus communis, Meligethes spp. such as M. aeneus; Melolontha spp. such as M. hippocastani, M. melolontha; Metamasius hemipterus, Microtheca spp., Migdolus spp. such as M. fryanus, Monochamus spp. such as M. alternatus; Naupactus xanthographus, Niptus hololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetoni a jucunda, Phaedon spp. such as P. brassicae, P. cochleariae; Phoracantha recurva, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp. such as P. helleri; Phyllotreta spp. such as P. chrysocephala, P. nemorum, P. striolata, P. vittula; Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psacothea hilaris, Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp. such as R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R. vulneratus; Saperda candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. such as T. castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp. such as X. pyrrhoderus; and, Zabrus spp. such as Z. tenebrioides;

insects from the order of Diptera e.g. Aedes spp. such as A. aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. maculopennis, A. minimus, A. quadrimaculatus, A. sinensis; Bactrocera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. macellaria; Chrysops atlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. such as C. hominivorax; Contarinia spp. such as C. sorghicola; Cordylobia anthropophaga, Culex spp. such as C. nigripalpus, C. pipiens, C. quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. platura, D. radicum; Dermatobia hominis, Drosophila spp. such as D. suzukii, Fannia spp. such as F. canicularis; Gastraphilus spp. such as G. intestinalis; Geomyza tipunctata, Glossina spp. such as G. fuscipes, G. morsitans, G. palpalis, G. tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifolii; Lucilia spp. such as L. caprin, L. cuprina, L. sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as M. destructor; Musca spp. such as M. autumnalis, M. domestica; Muscina stabulans, Oestrus spp. such as O. ovis; Opomyza florum, Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae, P. coarctata; Phytomyza gymnostoma, Prosimulium mixtum, Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis spp. such as R. cerasi, R. cingulate, R. indifferens, R. mendax, R. pomonella; Rivellia quadrifasciata, Sarcophaga spp. such as S. haemorrhoidalis; Simulium vittatum, Sitodiplosis mosellana, Stomoxys spp. such as S. calcitrans; Tabanus spp. such as T. atratus, T. bovinus, T. lineola, T. similis; Tannia spp., Thecodiplosis japonensis, Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp;

insects from the order of Thysanoptera for example, Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S. citri, S. dorsalis, S. perseae; Stenchaetothrips spp, Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp. such as T. imagines, T. hawaiiensis, T. oryzae, T. palmi, T. parvispinus, T. tabaci;

insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. hilare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Adelphocoris spp., such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Aulacorthum solani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses, Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii; Aphis spp. such as A. craccivora, A. fabae, A. forbesi, A. gossypii, A. grossulariae, A. maidiradicis, A. pomi, A. sambuci, A. schneideri, A. spiraecola; Arboridia apicalis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacaspis yasumatsui, Aulacorthum solani, Bactericera cockerelli (Paratrioza cockerelli), Bemisia spp. such as B. argentifolii, B. tabaci (Aleurodes tabaci); Blissus spp. such as B. leucopterus; Brachycaudus spp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola; Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae, Cacopsylla spp. such as C. fulguralis, C. pyricola (Psylla piri); Calligypona marginata, Calocoris spp., Campylomma livida, Capitophorus horni, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimex spp. such as C. hemibterus, C. lectularius; Coccomytilus halli, Coccus spp. such as C. hesperidum, C. pseudomagnoliarum, Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurodes spp. such as D. citrifoli; Dalbulus maidis, Diaphorina spp. such as D. citri; Diaspis spp. such as D. bromeliae; Dichelops furcatus, Diconocoris hewetti, Doralis spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp. such as D. plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani, Dysdercus spp. such as D. cingulatus, D. intermedius; Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. such as E. fabae, E. solana; Epidiaspis leperii, Eriosoma spp. such as E. lanigerum, E. pyricola; Erythroneura spp., Eurygaster spp. such as E. integriceps; Euscelis bilobatus, Euschistus spp. such as E. heros, E. impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp. such as H. halys; Heliopeltis spp., Homalodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, Icerya spp. such as I. purchase; Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. such as L. ulmi; Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L. hesperus, L. lineolaris, L. pratensis; Maconellicoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. such as M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae, Metcafiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus spp. such as M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia ribis-nigri, Neotoxoptera formosana, Neomegalotomus spp, Nephotettix spp. such as N. malayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp. such as N. viridula; Nilaparvata lugens, Nysius huttoni, Oebalus spp. such as O. pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hyalinipennis, Parabemisia myricae, Parlatoria spp., Parthenolecanium spp. such as P. corni, P. persicae; Pemphigus spp. such as P. bursarius, P. populivenae; Peregrinus maidis, Perkinsiella saccharicida, Phenacoccus spp. such as P. aceris, P. gossypii; Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. such as P. devastatrix, Piesma quadrata, Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentagon, Pseudococcus spp. such as P. comstocki; Psylla spp. such as P. mali; Pteromalus spp., Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R. padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaptocoris spp., Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis, Spissistilus festinus (=Stictocephala festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai, Tenalaphara malayensis, Tetraleurodes perseae, Therioaphis maculate, Thyanta spp. such as T. accerra, T. perditor, Tibraca spp., Tomaspis spp., Toxoptera spp. such as T. aurantii; Trialeurodes spp. such as T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifolii,

Insects from the order Hymenoptera for example Acanthomyops interjectus, Athalia rosae, Atta spp. such as A. capiguara, A. cephalotes, A. cephalotes, A. laevigata, A. robusta, A. sexdens, A. texana, Bombus spp., Brachymyrmex spp., Camponotus spp. such as C. floridanus, C. pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp, Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Dorymyrmex spp., Dryocosmus kuriphilus, Formica spp., Hoplocampa spp. such as H. minuta, H. testudinea; Iridomyrmex humilis, Lasius spp. such as L. niger, Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina longicornis, Paravespula spp., such as P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. such as P. megacephala; Pogonomyrmex spp. such as P. barbatus, P. californicus, Polistes rubiginosa, Prenolepsis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenopsis spp. such as S. geminata, S. invicta, S. molesta, S. richten, S. xyloni, Sphecius speciosus, Sphex spp., Tapinoma spp. such as T. melanocephalum, T. sessile; Tetramorium spp. such as T. caespitum, T. bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as V. squamosal; Wasmannia auropunctata, Xylocopa sp;

Insects from the order Orthoptera for example Acheta domesticus, Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. such as G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraussaria angulifera, Locusta spp. such as L. migratoria, L. pardalina; Melanoplus spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus; Nomadacris septemfasciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. such as S. americana, S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and Zonozerus variegatus;

Pests from the Class Arachnida for example Acari, e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A. americanum, A. variegatum, A. maculatum), Argas spp. such as A. persicu), Boophilus spp. such as B. annulatus, B. decoloratus, B. microplus, Dermacentor spp. such as D. silvarum, D. andersoni, D. variabilis, Hyalomma spp. such as H. truncatum, Ixodes spp. such as I. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R. sanguineus, R. appendiculatus, Rhipicephalus evertsi, Rhizoglyphus spp., Sarcoptes spp. such as S. Scabiei; and Family Eriophyidae including Aceria spp. such as A. sheldoni, A. anthocoptes, Acallitus spp., Aculops spp. such as A. lycopersici, A. pelekassi; Aculus spp. such as A. schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora; Eriophytes ribis and Eriophyes spp. such as Eriophyes sheldoni, Family Tarsonemidae including Hemitarsonemus spp., Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemus spinki; Family Tenuipalpidae including Brevipalpus spp. such as B. phoenicis; Family Tetranychidae including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T. pacificus, T. phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychus spp. such as P. ulmi, P. citri; Metatetranychus spp. and Oligonychus spp. such as O. pratensis, O. perseae, Vasates lycopersici; Raoiella indica, Family Carpoglyphidae including Carpoglyphus spp.; Penthaleidae spp. such as Halotydeus destructor, Family Demodicidae with species such as Dermodex spp.; Family Trombicidea including Trombicula spp.; Family Macronyssidae including Ornothonyssus spp.; Family Pyemotidae including Pyemotes tritici; Tyrophagus putrescentiae; Family Acaridae including Acarus siro; Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles reclusa;

Pests from the Phylum Nematoda, for example, plant parasitic nematodes such as root-knot nematodes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H. schachtii, H. trifolii; Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Aphelenchoides spp. such as A. besseyi; Sting nematodes, Belonolaimus spp. such as B. longicaudatus; Pine nematodes, Bursaphelenchus spp. such as B. lignicolus, B. xylophllus; Ring nematodes, Criconema spp., Criconemella spp. such as C. xenoplax and C. ornata; and, Criconemoides spp. such as Criconemoides informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp. such as D. destructor, D. dipsaci; Awl nematodes, Dolichodorus spp.; Spiral nematodes, Heliocotylenchus multicinctus; Sheath and sheathoid nematodes, Hemicycliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknot nematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. such as L. elongatus; Lesion nematodes, Pratylenchus spp. such as P. brachyurus, P. neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp. such as R. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform nematodes, Rotylenchus spp. such as R. robustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T. obtusus, T. primitivus; Paratrichodorus spp. such as P. minor; Stunt nematodes, Tylenchorhynchus spp. such as T. claytoni, T. dubius; Citrus nematodes, Tylenchulus spp. such as T. semipenetrans; Dagger nematodes, Xiphinema spp.; and other plant parasitic nematode species;

Insects from the order Isoptera for example Calotermes flavicollis, Coptotermes spp. such as C. formosanus, C. gestroi, C. acinaciformis; Cornitermes cumulans, Cryptotermes spp. such as C. brevis, C. cavifrons; Globitermes sulfureus, Heterotermes spp. such as H. aureus, H. longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp., Incisitermes spp. such as I. minor, I. Snyder, Marginitermes hubbardi, Mastotermes spp. such as M. darwiniensis Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. such as Z. angusticollis, Z. nevadensis, Reticulitermes spp. such as R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. santonensis, R. virginicus; Termes natalensis,

Insects from the order Blattaria for example Blatta spp. such as B. orientails, B. lateralis; Blattella spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchlora nivea, Periplaneta spp. such as P. americana, P. australasiae, P. brunnea, P. fuligginosa, P. japonica; Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis floridana, Pycnoscelus surinamensis,

Insects from the order Siphonoptera for example Cediopsylla simples, Ceratophyllus spp., Ctenocephalides spp. such as C. felis, C. canis, Xenopsylla cheopis, Pulex irritans, Trichodectes canis, Tunga penetrans, and Nosopsyllus fasciatus,

Insects from the order Thysanura for example Lepisma saccharin, Ctenolepisma urbana, and Thermobia domestica,

Pests from the class Chilopoda for example Geophilus spp., Scutigera spp. such as Scutigera coleoptrata;

Pests from the class Diplopoda for example Blaniulus guttulatus, Julus spp., Narceus spp.,

Pests from the class Symphyla for example Scutigerella immaculata,

Insects from the order Dermaptera, for example Forficula auricularia,

Insects from the order Collembola, for example Onychiurus spp., such as Onychiurus armatus,

Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber,

Insects from the order Phthiraptera, for example Damalinia spp., Pediculus spp. such as Pediculus humanus capitis, Pediculus humanus corporis, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis; Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,

Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp.; class Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., OpSthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

The compounds of the invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the invention also relates to the use of a compound of the invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites. Furthermore, the invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the invention.

The present invention also relates to the non-therapeutic use of compounds of the invention for treating or protecting animals against infestation and infection by parasites. Moreover, the invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.

The compounds of the invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the invention relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the invention.

The invention also relates to the non-therapeutic use of compounds of the invention for controlling or combating parasites. Moreover, the invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.

The compounds of the invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds of the invention can be applied to any and all developmental stages.

The compounds of the invention can be applied as such or in form of compositions comprising the compounds of the invention.

The compounds of the invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.

The compounds of the invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally. The compounds of the invention can be systemically or non-systemically effective.

The application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.

As used herein, the term “contacting” includes both direct contact (applying the compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at it's locus for the latter) and indirect contact (applying the compounds/compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of the compounds of the invention.

The term “locus” means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.

As used herein, the term “parasites” includes endo- and ectoparasites. In some embodiments of the invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

The compounds of the invention are especially useful for combating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria-Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus simills; lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae; Actinedida (Prostigmata) und Acaridida (Astigmata), e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp; Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp., and Arilus critatus; Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp.; Rhabditida, e.g. Rhabditis spp., Strongyloides spp., Helicephalobus spp.; Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capiliaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracunculus medinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofflari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp.; Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenoleps spp..

As used herein, the term “animal” includes warm-blooded animals (including humans) and fish. Preferred are mammals, such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Particularly preferred are domestic animals, such as dogs or cats.

In general, “parasiticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

Generally, it is favorable to apply the compounds of the invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.

The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are:

-   -   Solutions such as oral solutions, concentrates for oral         administration after dilution, solutions for use on the skin or         in body cavities, pouring-on formulations, gels;     -   Emulsions and suspensions for oral or dermal administration;         semi-solid preparations;     -   Formulations in which the active compound is processed in an         ointment base or in an oil-in-water or water-in-oil emulsion         base;     -   Solid preparations such as powders, premixes or concentrates,         granules, pellets, tablets, boluses, capsules; aerosols and         inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preservetives, and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile.

Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on. Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.

Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in-oil type or of the oil-in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.

Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form. Suitable auxiliaries for this purpose are known in the art.

The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the invention.

Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 percent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 percent by weight, most preferably from 5 to 40 percent by weight.

Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 percent by weight, preferably of 1 to 50 percent by weight.

Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 percent by weight, preferably of 0.05 to 0.9 percent by weight, very particularly preferably of 0.005 to 0.25 percent by weight.

Topical application may be conducted with compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which release compounds of the invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

EXAMPLES Preparation Examples

With appropriate modification of the starting materials, the procedures as described in the preparation examples below were used to obtain further compounds of formula I. The compounds obtained in this manner are listed in the table that follows, together with physical data.

Compounds can be characterized e.g. by coupled High Performance Liquid Chromatography/mass spectrometry (HPLC/MS), by 1H-NMR and/or by their melting points.

Analytical HPLC—Method 1: Agilent Eclipse Plus C18, 50×4.6 mm, ID 5 μm; Elution: A=10 mM Amm. Formate (0.1% Formic Acid), B=Acetonitrile (0.1% Formic Acid), Flow=1.2 ml/min. at 30° C.; Gradient: 10% B to 100% B-3 min, hold for 1 min, 1 min-10% B. Run Time=5.01 min.

Analytical HPLC—Method 2: Kinetex XB C18 1.7μ 50×2.1 mm; A=Water+0.1% TFA, B=Acetonitrile, Flow=0.8 ml/min-1.0 ml/min in 1.5 min. at 60° C.; Gradient: 5% B to 100% B-1.5 min.

1H-NMR: The signals are characterized by chemical shift (ppm, δ [delta]) vs. tetramethylsilane respectively, CDCl3 for 13C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m=multiplet, q=quartet, t=triplet, d=doublet and s=singlet.

Abbreviations used are: d for day(s), h for hour(s), min for minute(s), r.t./room temperature for 20-25° C., Rt for retention time; DMSO for dimethyl sulfoxide, OAc for acetate, EtOAc for ethyl acetate, THF for tetrahydrofuran, DMF for N,N-Dimethylformamide, ACN for acetonitrile, DCM for dichloromethane, TEA for triethylamine and t-BuOH for tert-butanol.

Example C-1 N-[5-[4-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-1)

Step-1: Synthesis of 5-(4-bromophenyl)-2-methyl-pyrazol-3-amine

To a stirred solution of methyl 3-(4-bromophenyl)-3-oxo-propanenitrile (3.6 g) in ethanol (30 mL) was added methylhydrazine 85% in water (3.6 mL) at ambient temperature. The reaction mixture was heated at 70° C. for 16 h. After completion of the reaction ethanol was removed under reduced pressure, crude was dissloved in water (50 mL). The mixture was extracted with EtOAc and the organic extracts dried over anhydrous sodium sulphate and evaporated in vacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (2.0 g). HPLC/MS (method 1): Rt: 1.58 min; m/z=254 (M+2)+.

Step-2: Synthesis of N-[5-(4-bromophenyl)-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy) benzamide

To a stirred solution of 5-(4-bromophenyl)-2-methyl-pyrazol-3-amine (1.75 g) in DCM:pyridine (1:1, 20 mL) was added 4-(trifluoromethoxy)benzoyl chloride (1.871 g) at 0° C. The reaction mixture was stirred at ambient temaperature for 2 h. The reaction mixture was dissloved in water (100 mL).The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (1.9 g). HPLC/MS (method 1): Rt: 2.05 min; m/z=442 (M+2)+.

Step-3: Synthesis of N-[2-methyl-5-(4-vinylphenyl)pyrazol-3-yl]-4-(trifluoromethoxy) benzamide

A solution of N-[5-(4-bromophenyl)-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.5 g) in toulene (10 mL) was degassed with nitrogen gas. Tri-n-butyl vinyl tin (0.54 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 g) were subsequently added and the mixture was heated at 110° C. for 4 h. The mixture was subsequently cooled to ambient temperature, diluted with water and extracted with EtOAc. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure and resultant residue subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to get the title compound as a solid (0.35 g). HPLC/MS (method 1): Rt: 2.04 min; m/z=388 (M+1)+.

Step-4: Synthesis of N-[5-(4-formylphenyl)-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy) benzamide

To a stirred solution of N-[2-methyl-5-(4-vinylphenyl)pyrazol-3-yl]-4-(trifluoromethoxy) benzamide (0.3 g) in 1,4-dioxane (4 mL) were added a solution of osmium tetroxide (0.004 g) in water (1 mL), sodium periodate (0.364 g). The mixture was stirred for 4 h and sodium sulfite solution (0.5% in Water) was subsequently added and the mixture was extracted with EtOAc. The organic extracts dried over sodium sulfate, and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (0.15 g).

Step-5: Synthesis of N-[5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-1)

A mixture of N-[5-(4-formylphenyl)-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.9 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.532 g) in ethanol (10 mL) was heated at 85° C. for 16 h. The mixture was cooled to ambient temperature and the precipitated solids were filtered and subjected to acidic alumina column chromatography using a gradient of DCM and methanol as eluent to afford the title compound as a solid (0.8 g).

HPLC/MS (method 1): Rt: 2.04 min; m/z=579 (M−1)+; 1H NMR (500 MHz, DMSO-d6) δ 11.78 (s, 1H), 10.57 (s, 1H), 10.02 (s, 1H), 8.19-8.11 (m, 3H), 7.93 (d, J=8.3 Hz, 2H), 7.84 (d, J=8.4 Hz, 2H), 7.61-7.55 (m, 2H), 7.40-7.27 (m, 2H), 7.25-7.20 (m, 2H), 6.84 (s, 1H), 3.79 (s, 3H), 3.15 (m, J=6.9 Hz, 1H), 1.20 (d, J=6.9 Hz, 6H).

Example C-2 N-[5-[4-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy) benzamide (C-2)

To a stirred mixture of N-[5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.345 g), methyl 2-bromoacetate (0.136 g) in ethanol (10 mL) was added sodium acetate (0.073 g) at 0° C. The mixture was stirred at ambient temperature for 16 h. Water (50 mL) was subsequently added. The mixture was extracted with EtOAc and the organic extracts dried over anhydrous sodium sulphate and evaporated invacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (0.15 g).

HPLC/MS (method 1): Rt: 2.09 min; m/z=621 (M+1)+; 1H NMR (300 MHz, DMSO-d6) δ 10.58 (s, 1H), 8.33 (s, 1H), 8.18-8.08 (m, 2H), 7.87 (d, J=8.3 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.63-7.41 (m, 4H), 7.40-7.22 (m, 2H), 6.82 (s, 1 H), 4.26 (d, J=17.4 Hz, 1H), 4.13 (d, J=17.4 Hz, 1H), 3.78 (s, 3H), 2.79 (m, J=6.8 Hz, 1H), 1.15 (t, J=7.3 Hz, 6H).

Example C-3 1-(2-isopropylphenyl)-3-[(E)-[4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]phenyl]methyleneamino]thiourea (C-3)

Step-1: Synthesis of methyl 4-(5-amino-1-methyl-pyrazol-3-yl)benzoate

To a stirred solution of methyl 4-(2-cyanoacetyl)benzoate (3.5 g) in ethanol (35.0 mL) was added methylhydrazine 85% in water (3.5 mL) at ambient temperature. The reaction mixture was heated at 70° C. for 16 h. After completion of the reaction ethanol was removed under reduced pressure, crude was dissolved in water (50 mL). The mixture was extracted with EtOAc and the organic extracts dried over anhydrous sodium sulphate and evaporated in vacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (3.0 g). 1H NMR (300 MHz, DMSO-d6) δ 7.99-7.86 (m, 2H), 7.79 (m, 2H), 5.79 (s, 1H), 5.35 (s, 2H), 3.84 (s, 3H), 3.59 (s, 3H).

Step-2: Synthesis of methyl 4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]benzoate

To a stirred solution of methyl 4-(5-amino-1-methyl-pyrazol-3-yl)benzoate (1.75 g) in DMF (20.0 mL), was added 1-(bromomethyl)-4-(trifluoromethoxy)benzene (2.12 g) and potassium carbonate (2.08 g). The mixture was heated at 80° C. for 16 h and subsequently cooled to ambient temperature. 200 mL of water was added, and the mixture extracted with EtOAc. The organic extracts were dried over anhydrous sodium sulphate, evaporated invacuo and the resultant solid was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and Heptane to obtain the title compound as a solid. (1.60 g). 1H NMR (300 MHz, DMSO-d6) δ 7.97-7.89 (m, 2H), 7.82-7.74 (m, 2H), 7.59-7.49 (m, 2H), 7.37-7.28 (m, 2H), 6.32 (t, J=6.0 Hz, 1H), 4.30 (d, J=5.9 Hz, 2H), 3.84 (s, 3H), 3.66 (s, 3H).

Step-3: Synthesis of [4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]phenyl]methanol

A solution of methyl 4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]benzoate (1.60 g) in THF (16.0 mL) and ethanol (6.0 mL), was added 2 M solution of lithium borohydride in THF (3.94 mL) at 0° C. and the mixture was stirred at rt for 16 h. The mixture was subsequently cooled to ambient temperature, quenched with saturated ammonium chloride solution (10.0 mL) and extracted with EtOAc. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure and resultant residue subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to get the title compound as a solid (1.20 g). 1H NMR (300 MHz, DMSO-d6) δ 7.64-7.50 (m, 4H), 7.38-7.22 (m, 4H), 6.21 (t, J=6.0 Hz, 1H), 5.73 (s, 1H), 5.13 (t, J=5.7 Hz, 1H), 4.47 (d, J=5.7 Hz, 2H), 4.29 (d, J=5.9 Hz, 2H), 3.62 (s, 3H).

Step-4: Synthesis of 4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]benzaldehyde

To a stirred solution of [4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]phenyl]methanol (0.650 g) in DMSO (6.0 mL), were added triethyl amine (0.260 g), sulfur trioxide pyridine complex (0.329 g). The mixture was stirred for 4 h and, water (20.0 mL) was subsequently added and the mixture was extracted with EtOAc. The organic extracts dried over sodium sulfate, and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (0.400 g). HPLC/MS (method 1): Rt: 1.926 min; m/z=374 (M−1)+.

Step-5: Synthesis of 1-(2-isopropylphenyl)-3-[(E)-[4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]phenyl]methyleneamino]thiourea (C-3)

A mixture of 4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]benzaldehyde (0.110 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.067 g) in ethanol (10.0 mL) was heated at 85° C. for 16 h. The mixture was cooled to ambient temperature and the precipitated solids were filtered and subjected to acidic alumina column chromatography using a gradient of DCM and methanol as eluent to afford the title compound as a solid (0.125 g).

HPLC/MS (method 1): Rt: 2.115 min; m/z=567.1 (M+1)+; 1H NMR (300 MHz, DMSO-d6) δ 11.74 (s, 1 H), 9.97 (s, 1 H), 8.12 (s, 1H), 7.94-7.77 (m, 2H), 7.78-7.60 (m, 2H), 7.62-7.45 (m, 2H), 7.45-7.28 (m, 3H), 7.27-7.07 (m, 3H), 6.27 (t, J=6.0 Hz, 1 H),), 5.84 (s,1 H), 4.30 (d, J=5.8 Hz, 2H), 3.64 (s, 3H), 3.12 (p, J=6.8 Hz, 1H), 1.18 (d, J=6.9 Hz, 6H).

Example C-5 1-(2-isopropylphenyl)-3-[(E)-[4-[1-methyl-5-[[4-(trifluoromethoxy) benzenecarboximidoyl]amino]pyrazol-3-yl]phenyl]methyleneamino]thiourea (C-5)

Step-1: Synthesis of 5-(4-bromophenyl)-2-methyl-pyrazol-3-amine

To a stirred solution of methyl 3-(4-bromophenyl)-3-oxo-propanenitrile (3.6 g) in ethanol (30.0 mL) was added methylhydrazine 85% in water (3.6 mL) at ambient temperature. The reaction mixture was heated at 70° C. for 16 h. After completion of the reaction ethanol was removed under reduced pressure, crude was dissolved in water (50 mL). The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (2.0 g). HPLC/MS (method 1): Rt: 1.58 min; m/z=254 (M+2)+.

Step-2: Synthesis of N-[5-(4-bromophenyl)-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamidine

To a stirred solution of 5-(4-bromophenyl)-2-methyl-pyrazol-3-amine (1.20 g) in toulene was added(trifluoromethoxy)benzonitrile (1.06 g) and a 2 M solution of trimethyl aluminium in toluene (4.76 mL). The mixture was heated at 110° C. for 2 h and subsequently cooled to ambient temperature. A solution of 2.0 N HCl was added dropwise and the mixture extracted with EtOAc. The organic extracts were dried over anhydrous sodium sulphate, evaporated in vacuo and the resultant solid was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid. (1.20 g). HPLC/MS (method 1): Rt: 2.10 min; m/z=438 (M−1)+.

Step-3: Synthesis of N-[2-methyl-5-(4-vinylphenyl)pyrazol-3-yl]-4-(trifluoromethoxy) benzamidine was achieved following method similar to step 3 of C-1. HPLC/MS (method 1): Rt: 1.98 min; m/z=387 (M+1)+.

Step-4: Synthesis of N-[5-(4-formylphenyl)-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamidine was achieved following method similar to step 4 of C-1. HPLC/MS (method 1): Rt: 1.86 min; m/z=387 (M−1)+.

Step-5: Synthesis of 1-(2-isopropylphenyl)-3-[(E)-[4-[1-methyl-5-[[4-(trifluoromethoxy)benzenecarboximidoyl]amino]pyrazol-3-yl]phenyl]methyleneamino]thiourea(C-5) was achieved following method similar to step 5 of C-1.

HPLC/MS (method 1): Rt: 2.10 min; m/z=579.95 (M+1)+; 1H NMR (300 MHz, DMSO-d6) δ 11.78 (s, 1H), 10.00 (s, 1H), 8.17 (d, J=9.2 Hz, 3H), 7.92 (d, J=8.3 Hz, 2H), 7.85 (d, J=8.2 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 7.34-7.15 (m, 7H), 6.71 (s, 1H), 3.78 (s,1H), 3.14 (p, J=6.8 Hz, 1H), 1.20 (d, J=6.9 Hz, 6H).

Example C-6 Synthesis of N-[5-[4-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy) benzamidine (C-6) was achieved following method similar step of C-2.

HPLC/MS (method 1): Rt: 2.16 min; m/z=620 (M+1)+; 1H NMR (500 MHz, DMSO-d6) δ 8.31 (s, 1H), 8.18 (d, J=8.7 Hz, 2H), 7.89 (d, J=8.1 Hz, 2H), 7.76 (d, J=8.1 Hz, 2H), 7.56-7.42 (m, 4H), 7.34 (td, J=7.5, 1.7 Hz, 2H), 7.27 (dd, J=7.9, 1.4 Hz, 2H), 6.69 (s, 1 H), 4.36-4.09 (m, 2H), 3.79 (s, 3H), 2.80 (p, J=6.8 Hz, 1H), 1.16 (dd, J=12.9, 6.9 Hz, 6H).

Example C-10 1-(2-isopropylphenyl)-3-[(E)-[4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methoxy]pyrazol-3-yl]phenyl]methyleneamino]thiourea (C-10)

Step-1: Synthesis of 5-(4-bromophenyl)-2-methyl-pyrazol-3-ol

To a stirred solution of ethyl 3-(4-bromophenyl)-3-oxo-propanoate (2.0 g) in acetic acid (20.0 mL), was added methylhydrazine 85% in water (3.0 mL) at ambient temperature. The reaction mixture was heated at 70° C. for 16 h. After completion of the reaction Acetic acid was removed under reduced pressure, crude was dissolved in water (50 mL). The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (0.90 g). HPLC/MS (method 1): Rt: 1.54 min; m/z=252.7 (M+1)+.

Step-2: Synthesis of 3-(4-bromophenyl)-1-methyl-5-[[4-(trifluoromethoxy) phenyl]methoxy]pyrazole.

To a stirred solution of 5-(4-bromophenyl)-2-methyl-pyrazol-3-ol (0.800 g) in DMF, was added sodium hydride (0.169 g, 60% dispersion in mineral), and a 1-(bromomethyl)-4-(trifluoromethoxy)benzene (0.887 g). The mixture was stirred at rt for 16 h. Water (50.0 mL) was subsequently added and the mixture extracted with EtOAc. The organic extracts were dried over anhydrous Sodium sulphate, evaporated in vacuo and the resultant solid was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid. (0.400 g). HPLC/MS (method 1): Rt: 2.20 min; m/z=428.9 (M+1)+.

Step-3: Synthesis of 1-methyl-5-[[4-(trifluoromethoxy)phenyl]methoxy]-3-(4-vinylphenyl)pyrazole was achieved following method similar to step 3 of C-1. H PLC/MS (method 1): Rt: 2.20 min; m/z=373 (M−1)+.

Step-4: Synthesis of 4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methoxy]pyrazol-3-yl]benzaldehyde was achieved following method similar to step 4 of C-1. H PLC/MS (method 1): Rt: 2.06 min; m/z=375 (M−1)+.

Step-5: Synthesis of 1-(2-isopropylphenyl)-3-[(E)-[4-[1-methyl-5-[[4-(trifluoromethoxy) phenyl]methoxy]pyrazol-3-yl]phenyl]methyleneamino]thiourea (C-10) was achieved following method similar to step 5 of C-1.

HPLC/MS (method 1): Rt: 2.251 min; m/z=567.90 (M+1)+; 1H NMR (500 MHz, DMSO-d6) δ 11.78 (s, 1 H), 10.00 (s, 1 H), 8.15 (s, 1 H), 7.91 (d, J=8.3 Hz, 2H), 7.79-7.74 (m, 2H), 7.69-7.63 (m, 2H), 7.46-7.40 (m, 2H), 7.40-7.34 (m, 1H), 7.30 (ddd, J=8.0, 5.4, 3.3 Hz, 1H), 7.26-7.19 (m, 2H), 6.37 (s, 1H), 5.27 (s, 2H), 3.64 (s, 3H), 3.13 (h, J=6.8 Hz, 1H), 1.20 (d, J=6.8 Hz, 6H).

Example C-12 (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methoxy]pyrazol-3-yl]phenyl]methyleneamino]thiazolidin-4-one (C-12)

To a stirred mixture of 4-[1-methyl-5-[[4-(trifluoromethoxy)phenyl]methoxy]pyrazol-3-yl]benzaldehyde(0.120 g), (2E)-3-amino-2-(2-isopropylphenyl)imino-thiazolidin-4-one (0.095 g) in acetic acid (3.0 mL) was stirred at ambient temperature for 4 h. Water (50.0 mL) was subsequently added. The mixture was extracted with EtOAc and the organic extracts dried over anhydrous sodium sulphate and evaporated invacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (0.150 g).

HPLC/MS (method 1): Rt: 2.33 min; m/z=608 (M+1)+; 1H NMR (500 MHz, DMSO-d6) δ 9.05 (s, 1 H), 7.97-7.87 (m, 4H), 7.70-7.64 (m, 2H), 7.46-7.40 (m, 2H), 7.31 (dd, J=7.7, 1.6 Hz, 1H), 7.18 (td, J=7.5, 1.6 Hz, 1H), 7.12 (td, J=7.5, 1.5 Hz, 1H), 6.86 (dd, J=7.8, 1.4 Hz, 1H), 6.42 (s, 1H), 5.29 (s, 2H), 4.15 (s, 2H), 3.66 (s, 3H), 3.00 (hept, J=6.9 Hz, 1H), 1.14 (d, J=6.9 Hz, 6H).

Example C-15 N-[5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide

Step 1: Synthesis of N-(2,4-dimethylpyrazol-3-yl)-4-(trifluoromethypenzamide

To a stirred solution of 4-(trifluoromethyl)benzoic acid (2.5 g) in DMF (75 mL) was added HATU (10.0 g) and DIPEA (6.771 mL) at 0° C. After stirring the reaction mixture for 1 h, 2,4-di-methylpyrazol-3-amine (1.754 g) was added at 0° C. The mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with brine (NaCl aq. solution) and extracted with EtOAc. The organic phase was dried over sodium sulfate, concentrated under reduced pressure and resultant residue subjected to silica gel flash column chromatography, eluting with a gradient of MeOH and DCM to obtain the title compound as a solid (3.5 g). HPLC/MS (method 2): Rt: 0.983 min; m/z=283.9 (M+1)+.

Step 2: Synthesis of N-(5-iodo-2,4-dimethyl-pyrazol-3-yl)-4-(trifluoromethyl)benzamide

To a stirred solution of N-(2,4-dimethylpyrazol-3-yl)-4-(trifluoromethyl)benzamide (1.0 g) in DMF (30.0 mL) was added N-iodosuccinimide. The mixture was stirred for 16 h at 60° C. and water (30.0 mL) was subsequently added and the mixture was extracted with EtOAc and aq. NaHCO3. The organic phase was dried over sodium sulfate, and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and cyclohexane to obtain the title compound as a solid (0.5 g).

HPLC/MS (method 2): Rt: 1.118 min; m/z=409.7 (M+1)+.

Step 3: Synthesis of N-[5-(4-formylphenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide

A solution of N-(5-iodo-2,4-dimethyl-pyrazol-3-yl)-4-(trifluoromethyl)benzamide (0.490 g), (4-formylphenyl)boronic acid (0.269 g), potassium carbonate (0.414 g), water (1 mL) in 1,2-di-methoxyethane (20 mL) was set under argon atmosphere. Pd(dppf)Cl2 (0.044 g) was added to the reaction mixture and stirred for 16 h at 80° C. The solvent was removed under reduced pressure and the mixture was extracted with EtOAc and water. The organic phase was dried over sodium sulfate, and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and cyclohexane to obtain the title compound as a solid (0.270 g). HPLC/MS (method 2): Rt: 1.122 min; m/z=387.8 (M+1)+.

Step 4: Synthesis of N-[5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethypenzamide was achieved following method similar to step 5 of C-1.

HPLC/MS (method 2): Rt: 1.318 min; m/z=579.0 (M+1)+. 1H NMR (400 MHz, Chloroform-d) δ 9.46 (s, 1 H), 8.99 (s, 1 H), 8.20 (d, J=8.0 Hz, 2H), 7.86-7.78 (m, 3H), 7.75 (d, J=8.2 Hz, 2H), 7.68 (d, J=8.1 Hz, 2H), 7.61 (d, J=7.7 Hz, 1H), 7.41-7.26 (m, 4H), 3.97 (s, 3H), 3.15 (p, J=6.9 Hz, 1H), 2.16 (s, 3H), 1.30 (s, 3H), 1.28 (s, 3H).

Example C-29 N-[2-ethyl-5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-29)

Step-1: Synthesis of 5-(4-bromophenyl)-2-ethyl-pyrazol-3-amine

To a stirred solution of 3-(4-bromophenyl)-3-oxo-propanenitrile (6 g) in ethanol (60.0 mL) were added ethylhydrazine dihydrochloride (4.27 g) and diisopropyl ethylamine (6.92 g) at ambient temperature. The reaction mixture was heated at 85° C. for 12 h and after completion of the reaction ethanol was removed under reduced pressure, crude was dissloved in water. The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo. The residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (6.2 g). HPLC/MS (method 1): Rt: 1.64 min; m/z=265.50 (M+1)+.

Step-2: Synthesis of N-[5-(4-bromophenyl)-2-ethyl-pyrazol-3-yl]-4-(trifluoromethoxy) benzamide was achieved following method similar to step 2 of C-1.

HPLC/MS (method 1): Rt: 2.069 min; m/z=455.15 (M+1)+.

Step-3: Synthesis of N-[2-ethyl-5-(4-vinylphenyl)pyrazol-3-yl]-4-(trifluoromethoxy) Benzamide was achieved following method similar to step 3 of C-1.

HPLC/MS (method 1): Rt: 2.027 min; m/z=401.55 (M+1)+.

Step-4: Synthesis of N[2-ethyl-5-(4-formylphenyl)pyrazol-3-yl]-4 (trifluoromethoxy) Benzamide was achieved following method similar to step 4 of C-1.

HPLC/MS (method 1): Rt: 1.909 min; m/z=403.45 (M+1)+.

Step-5: Synthesis of N-[2-ethyl-5-[4-[(E)-[(2 isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]pyrazol-3-yl]-4 (trifluoromethoxy)benzamide (C-29) was achieved following method similar to step 5 of C-1.

HPLC/MS (method 1): Rt: 2.112 min; m/z=592.70 (M−1)+.

Example C-32 Synthesis of N-[2-ethyl-5-[4-[(E)-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]oxyiminomethyl]phenyl]pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-32)

A mixture of N[2-ethyl-5-(4-formylphenyl)pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.4 g) and O-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]hydroxylamine (0.219 g) in ethanol (4.0 mL) was heated at 85° C. for 3 h. The mixture was cooled to ambient temperature and the solvent concentrated under reduced pressure and resultant residue subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (0.220 g).

HPLC/MS (method 1): Rt: 2.059 min; m/z=605 (M−1)+; 1H NMR (500 MHz, DMSO-d6) δ 10.52 (s, 1 H), 8.42 (s, 1 H), 8.17-8.10 (m, 2H), 7.91-7.81 (m, 2H), 7.72-7.67 (m, 2H), 7.61-7.55 (m, 2H), 6.81 (s, 1 H), 5.52 (d, J=2.1 Hz, 1 H), 4.11 (q, J=7.2 Hz, 2H), 3.80 (dd, J=3.3, 2.1 Hz, 1H), 3.56 (dq, J=9.5, 6.3 Hz, 1H), 3.46-3.36 (m, 10H), 3.05 (t, J=9.3 Hz, 1H), 1.38 (t, J=7.2 Hz, 3H), 1.18 (d, J=6.2 Hz, 3H).

Example C-33 Synthesis of [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-ethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate (C-33)

Step-1: Synthesis of 2-ethyl-5-(4-nitrophenyl)pyrazol-3-amine

To a stirred solution of 3-(4-nitrophenyl)-3-oxo-propanenitrile (1.0 g) in ethanol (10.0 mL) were added ethylhydrazine dihydrochloride (0.839 g) and diisopropyl ethylamine (1.359 g) at ambient temperature. The reaction mixture was heated at 85° C. for 12 h and after completion of the reaction ethanol was removed under reduced pressure, crude was dissloved in water. The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo. The residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (1.2 g). HPLC/MS (method 1): Rt: 1.557 min; m/z=231.8 (M−1)+.

Step-2: Synthesis of N-[2-ethyl-5-(4-nitrophenyl)pyrazol-3-yl]-4-(trifluoromethoxy) benzamide

To a stirred solution of 2-ethyl-5-(4-nitrophenyl)pyrazol-3-amine (1.2 g) in DCM, pyridine (12:3 mL) was added 4-(trifluoromethoxy)benzoyl chloride (1.276 g) at 0° C. The reaction mixture was stirred at ambient temaperature for 12 h. The reaction mixture was dissloved in water and the mixture was extracted with EtOAc. The organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo. The residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (2 g). HPLC/MS (method 1): Rt: 1.963 min; m/z=421 (M+1)+.

Step-3: Synthesis of N-[5-(4-aminophenyl)-2-ethyl-pyrazol-3-yl]-4-(trifluoromethoxy) benzamide

To a stirred solution of N-[2-ethyl-5-(4-nitrophenyl)pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (2.0 g) in Isopropyl alcohol (20.0 mL) were subsequently added bispinacolato diborane (3.76 g) and pottasium t-butoxide (0.639 g) and the mixture was heated at 110° C. for 4 h. The mixture was subsequently cooled to ambient temperature, diluted with water and extracted with EtOAc. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The resultant residue subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to get the title compound as a solid (1.8 g). HPLC/MS (method 1): Rt: 1.739 min; m/z=390.65 (M+1)+.

Step-4: Synthesis of (4-nitrophenyl) N-[4-[1-ethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate

To a stirred solution of N-[5-(4-aminophenyl)-2-ethyl-pyrazol-3-yl]-4-(trifluoromethoxy) Benzamide (2.0 g) in THF (20 mL) was added (4-nitrophenyl) carbonochloridate (1.136 g) and the mixture was stirred at 0° C. for 4 h. The reaction mixture was evaporated in vacuo. and the residue obtained was subjected to heptane tituration, filtered and evaporated under vacuo. to obtain the title compound as a solid (2.5 g).

Step-5: Synthesis of [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-ethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate (C-33)

To a mixture of (4-nitrophenyl) N-[4-[1-ethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate (1.0 g) and (2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-ol (0.446 g) in MeCN (10 mL) were subsequently added K3PO4 hydrate (0.763 g) and diisopropyl amine (0.464 g) at 0° C. The reaction mass was stirred at ambient temperature for 12 h. The mixture was diluted with water and extracted with EtOAc; and the organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The resultant residue subjected to Prep. HPLC to get the title compound as a solid (0.12 g). HPLC/MS (method 1): Rt: 1.909 min; m/z=622 (M+1)+; 1H NMR (300 MHz, DMSO-d6) δ 10.46 (s, 1H), 9.89 (s, 1H), 8.18-8.07 (m, 2H), 7.78-7.70 (m, 2H), 7.70-7.47 (m, 4H), 6.66 (s, 1H), 5.97 (d, J=2.1 Hz, 1H), 4.07 (q, J=7.2 Hz, 2H), 3.75 (t, J=2.7 Hz, 1H), 3.64 (dd, J=9.5, 6.1 Hz, 1H), 3.60-3.48 (m, 1H), 3.44 (d, J=5.9 Hz, 9H), 3.06 (t, J=9.3 Hz, 1H), 1.36 (t, J=7.2 Hz, 3H), 1.19 (d, J=6.2 Hz, 3H).

Example C-34

Step 1: Synthesis of N-[5-(4-bromophenyl)-2-ethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethoxy)benzamide

To a stirred solution of N-[5-(4-bromophenyl)-2-ethyl-pyrazol-3-yl]-4-(trifluoromethoxy) Benzamide (0.3 g) in N,N-Dimethylformamide (3 mL) were subsequently added methyl iodide (0.103 g) and Pottasium carbonate (0.182 g) at ambient temperature. The reaction mixture was heated at 85° C. for 6 h and after completion of the reaction, reaction mass was diluted with water. The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate; and evaporated in vacuo. The residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (0.24 g). HPLC/MS (method 1): Rt: 2.240 min; m/z=469.15 (M+1)+.

Step 2: Synthesis of N-[2-ethyl-5-(4-vinylphenyl)pyrazol-3-yl]-N-methyl-4-(trifluoromethoxy)benzamide was achieved following method similar to step 3 of C-1.

HPLC/MS (method 1): Rt: 2.176 min; m/z=415.55 (M+1)+.

Step 3: Synthesis of N-[2-ethyl-5-(4-formylphenyl)pyrazol-3-yl]-N-methyl-4-(trifluoromethoxy)benzamide was achieved following method similar to step 4 of C-1. HPLC/MS (method 1): Rt: 1.973 min; m/z=417.35 (M+1)+.

Step 4: Synthesis of N-[2-ethyl-5-[4-[(E)-[(2-isopropylphenyl) carbamothioylhydrazono]methyl]phenyl]pyrazol-3-yl]-N-methyl-4-(trifluoromethoxy) benzamide (C-34) was achieved following method similar to step 5 of C-1.

HPLC/MS (method 1): Rt: 2.144 min; m/z=608.50 (M+1)+; 1H NMR (500 MHz, DMSO-d6) δ 11.78 (s, 1H), 9.99 (s, 1H), 8.14 (s, 1H), 7.90 (d, J=8.1 Hz, 2H), 7.73 (d, J=7.9 Hz, 2H), 7.52 (s, 2H), 7.36 (d, J=7.7 Hz, 1H), 7.30 (ddd, J=8.0, 5.3, 3.4 Hz, 3H), 7.26-7.19 (m, 2H), 6.80 (s, 1H), 3.9-4 (s, 2H), 3.3 (s, 3H), 3.13 (p, J=6.9 Hz, 1H), 1.26 (s, 3H), 1.19 (d, J=6.9 Hz, 6H).

Example C-40 [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]phenyl]carbamate (C-40)

Step-1: Synthesis of 2-ethyl-5-(4-nitrophenyl)pyrazol-3-amine

To a stirred solution of 3-(4-nitrophenyl)-3-oxo-propanenitrile (1.3 g) in ethanol (25 mL) were added ethylhydrazine dihydrochloride (1.364 g) and diisopropyl ethylamine (2.65 g) at ambient temperature. The reaction mixture was heated at 85° C. for 12 h and after completion of the reaction ethanol was removed under reduced pressure, crude was dissloved in water. The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo. The residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (1.54 g). HPLC/MS (method 1): Rt: 0.816 min; m/z=232.9 (M+1)+.

Step-2: Synthesis of (E)-N-[2-ethyl-5-(4-nitrophenyl)pyrazol-3-yl]-1-[4 (trifluoromethoxy)phenyl]methanimine

To a stirred solution of 2-ethyl-5-(4-nitrophenyl)pyrazol-3-amine (1.54 g) in ethanol (20 mL) was added 4-(trifluoromethoxy)benzaldehyde (1.57 g) and the reaction mixture was stirred at 60° C. for 2 h. The precipitated product was filtered off under suction and triturated with Diisopropyl ether, product was filtered off and evaporated in vacuo to obtain the title compound as a solid (0.9 g). HPLC/MS (method 1): Rt: 1.484 min; m/z=404.8 (M+1)+.

Step-3: Synthesis of 2-ethyl-5-(4-nitrophenyl)-N-[[4-(trifluoromethoxy)phenyl]methyl]pyrazol-3-amine

To a stirred solution of (E)-N-[2-ethyl-5-(4-nitrophenyl)pyrazol-3-yl]-1-[4 (trifluoromethoxy)phenyl]methanimine (0.9 g) in ethanol (15 mL) at 0° C. was subsequently added sodium borohydride (0.126 g) and the mixture was stirred at ambient temperature for 4 h. The mixture was evaporated in vacuo, diluted with water and extracted with EtOAc. The organic extracts were dried over Sodium sulfate and concentrated under reduced pressure to get the title compound as a solid (0.77 g). HPLC/MS (method 1): Rt: 1.322 min; m/z=407 (M+1)+.

Step-4: Synthesis of 5-(4-aminophenyl)-2-ethyl-N-[[4-(trifluoromethoxy)phenyl]methyl]pyrazol-3-amine

To a stirred solution of 2-ethyl-5-(4-nitrophenyl)-N-[[4-(trifluoromethoxy) phenyl]methyl]pyrazol-3-amine (0.77 g) in methanol (30.0 mL) was subsequently added tin (II) chloride dihydrate (1.282 g) and mixture was stirred at 70° C. for 12 h. The mixture was diluted with 1 N NaOH solution and extracted with EtOAc. The organic extracts were dried over Sodium sulfate and concentrated under reduced pressure to obtain the title compound as a solid (0.71 g). HPLC/MS (method 1): Rt: 0.956 min; m/z=377 (M+1)+.

Step-5: Synthesis of (4-nitrophenyl) N-[4-[1-ethyl-5-[[4 (trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]phenyl]carbamate

To a stirred solution of 5-(4-aminophenyl)-2-ethyl-N-[[4 (trifluoromethoxy)phenyl]methyl]pyrazol-3-amine (0.71 g) in THF (8 mL) was added (4-nitrophenyl) carbonochloridate (0.380 g) and the mixture was stirred at 0° C. for 4 h. The reaction mixture was evaporated in vacuo. and the residue obtained was subjected to heptane tituration, filtered and evaporated under vacuo. to obtain the title compound as a solid (1 g).

HPLC/MS (method 1): Rt: 1.178 min; m/z=542.1 (M+1)+.

Step-6: Synthesis of [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]phenyl]carbamate (C-40)

To a mixture of (4-nitrophenyl) N-[4-[1-ethyl-5-[[4 (trifluoromethoxy)phenyl]methylamino]pyrazol-3-yl]phenyl]carbamate (0.3 g) and (2 R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-ol (0.137 g) in MeCN (9.0 mL) were subsequently added Tripotassium phosphate hydrate (0.294 g) and Diisopropyl amine (0.179 g) at 0° C. The reaction mass was stirred at ambient temperature for 12 h and the mixture was diluted with water and extracted with EtOAc. The organic extracts were dried over Sodium sulfate and concentrated under reduced pressure. The resultant residue subjected to Prep. HPLC to get the title compound as a solid (0.08 g) HPLC/MS (method 1): Rt: 1.111 min; m/z=609.2 (M+1)+.

Example C-47 Synthesis of 5-[4-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]-2-methyl-N-[4-(trifluoromethoxy)phenyl]pyrazole-3-carboxamide

Step 1: Synthesis of 5-(4-formylphenyl)-2-methyl-pyrazole-3-carboxylic acid was achieved following method similar to step 3 of C-15.

HPLC/MS (method 2): Rt: 0.857 min; m/z=231 (M+1)+.

Step 2: Synthesis of 5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-2-methyl-pyrazole-3-carboxylic acid was achieved following method similar to step 5 of C-1. H PLC/MS (method 2): Rt: 1.14 min; m/z=422 (M+1)+.

Step 3: Synthesis of 5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-2-methyl-pyrazole-3-carboxylic acid was achieved following method similar step of C-2. HPLC/MS (method 2): Rt: 1.22 min; m/z=462 (M+1)+.

Step 4: Synthesis of 5-[4-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]-2-methyl-N-[4-(trifluoromethoxy)phenyl]pyrazole-3-carboxamide was achieved following method similar to step 5 of C-1.

HPLC/MS (method 2): Rt: 1.48 min; m/z=621 (M+1)+.

Example C-52

Step-1: Synthesis of Ethyl 4-(4-bromophenyl)-2,4-dioxo-butanoate

To a stirred solution of 1-(4-bromophenyl)ethanone (5.0 g) in toluene (80.0 mL) was added sodium hydride (1.2 g) at 0° C. The reaction mixture was stirred at ambient temaperature for 10min. The reaction mixture cooled to 0° C. and diethyl oxalate (4.40 g) was added. The reaction mixture was heated at 50° C. for 3 h. The reaction mixture was quench with ammonium chloride solution (100 mL).The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (7.1g) HPLC/MS (method 1): Rt: 2.02 min; m/z=298.5 (M−1)+.

Step-2: Synthesis of Ethyl 5-(4-bromophenyl)-2-methyl-pyrazole-3-carboxylate

To a stirred solution of ethyl 4-(4-bromophenyl)-2,4-dioxo-butanoate (7.0 g) in ethanol (100 mL) was added acetic acid (2.0 mL) & methylhydrazine 85% in water (7.0 mL) at 0° C. The reaction mixture was heated at 90° C. for 4 h. After completion of the reaction ethanol was removed under reduced pressure, crude was dissloved in water (100 mL). The mixture was extracted with EtOAc and the organic extracts dried over anhydrous sodium sulphate and evaporated in vacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (4.0 g). HPLC/MS (method 1): Rt: 2.2 min; m/z=310 (M+1)+.

Step-3: Synthesis of [5-(4-bromophenyl)-2-methyl-pyrazol-3-yl]methanol

To a stirred solution of ethyl 5-(4-bromophenyl)-2-methyl-pyrazole-3-carboxylate (4.0 g) in THF (50 mL) was 1M solution of lithium aluminium hydride in THF (15.0 mL) at 0° C. The reaction mixture was stirred at ambient temaperature for 4h. The reaction mixture was quench with saturated sodium sulphate solution (100 mL).The mixture was extracted with EtOAc and the organic extracts dried over anhydrous sodium sulphate and evaporated in vacuo to obtain the title compound as a solid (3.2 g) H PLC/MS (method 1): Rt: 1.6 min; m/z=268 (M+1)+.

Step-4: Synthesis of 3-(4-bromophenyl)-5-(chloromethyl)-1-methyl-pyrazole

To a stirred solution of [5-(4-bromophenyl)-2-methyl-pyrazol-3-yl]methanol (0.4 g) in DCM (8.0 mL) was methanesulfonyl chloride (0.206 g) at 0° C. The reaction mixture was stirred at ambient temaperature for 4h. The reaction mixture was quench with water (40 mL). The mixture was extracted with EtOAc and the organic extracts dried over anhydrous Sodium sulphate and evaporated in vacuo to obtain the title compound as a solid (0.4 g). HPLC/MS (method 1): Rt: 2.02 min; m/z=286 (M+1)+.

Step-5: Synthesis of 3-(4-bromophenyl)-1-methyl-5[[4-(trifluoromethoxy)phenoxy]methyl]pyrazole

To a stirred solution of 3-(4-bromophenyl)-5-(chloromethyl)-1-methyl-pyrazole (0.350 g) in MeCN (4.0 mL) was added K2CO3 (0.333 g) and 4-(trifluoromethoxy)phenol (0.196 g) at ambient temperature. The reaction mixture was heated at 90° C. for 4h. The reaction mixture was dissloved in water (50 mL).The mixture was extracted with EtOAc and the organic extracts dried over anhydrous sodium sulphate and evaporated in vacuo and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to obtain the title compound as a solid (0.38 g). HPLC/MS (method 1): Rt: 2.2 min; m/z=428 (M+1)+.

Step-6: Synthesis of 1-methyl-5-[[4-(trifluoromethoxy)phenoxy]methyl]-3-(4-vinylphenyl)pyrazole was achieved following method similar to step 3 of C-1. HPLC/MS (method 1): Rt: 2.18 min; m/z=375 (M+1)+.

Step-7: Synthesis of 4-[1-methyl-5-[[4-(trifluoromethoxy)phenoxy]methyl]pyrazol-3-yl]benzaldehyde was achieved following method similar to step 4 of C-1.

HPLC/MS (method 1): Rt: 2.08 min; m/z=375 (M−1)+.

Step-8: Synthesis of 1-(2-isopropylphenyl)-3-[(E)-[4-[1-methyl-5-[[4-(trifluoromethoxy)phenoxy]methyl]pyrazol-3-yl]phenyl]methyleneamino]thiourea (C-52) was achieved following method similar to step 5 of C-1.

HPLC/MS (method 1): Rt: 2.1 min; m/z=566(M−1)+; 1H NMR (500 MHz, DMSO-d6) δ 11.80 (s, 1H), 10.02 (s, 1H), 8.15 (s, 1H), 7.93 (d, J=8.2 Hz, 2H), 7.84-7.79 (m, 2H), 7.36 (m,4H), 7.30 (m,4H), 6.95 (s, 1H), 5.25 (s, 2H), 3.91 (s, 3H), 3.13 (p, J=6.9 Hz, 1H), 1.19 (d, J=6.9 Hz, 6H).

Example C-57 Synthesis of N-[3-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-1H-pyrazol-5-yl]-4-(trifluoromethoxy)benzamide (C-57)

Step-1: Synthesis of methyl 4-(5-amino-1H-pyrazol-3-yl)benzoate

To a stirred solution of methyl 4-(2-cyanoacetyl)benzoate (2.4 g) in ethanol (35.0 mL) was added hydrazine hydrate (0.6 mL) at ambient temperature. The reaction mixture was heated at 80° C. for 3 h. The progress of the reaction was monitored by TLC. After the completion of reaction, the excess ethanol was removed. The reaction mixture was diluted with water (75 mL) then extracted with ethyl acetate (100 mL). The organic layer was dried over sodium sulphate and concentrated in vacuo to offer the desired product as solid (1.82 g).

1H NMR (500 MHz, DMSO-d6) δ 11.85 (bs, 1H), 7.95 (d, J=8.0 Hz, 2H), 7.80 (d, J=8.1 Hz, 2H), 5.80 (bs, 1H), 5.22 (bs, 2H), 3.86 (s, 3H).

Step 2: Synthesis of methyl 4-[5-[[4-(trifluoromethoxy)benzoyl]amino]-1H-pyrazol-3-yl]benzoate was achieved following method similar to step 2 of C-1. HPLC/MS (method 1): Rt: 1.867 min; m/z=406 (M+1)+.

Step 3: Synthesis of N-[3-[4-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl]-4-(trifluoromethoxy)benzamide

To a stirred solution of methyl 4-[5-[[4-(trifluoromethoxy)benzoyl]amino]-1H-pyrazol-3-yl]benzoate (0.5 g) in THF (10.0 mL) was added 1M LAH solution in THF (1.3 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 3h. The progress of the reaction was monitored by TLC analysis. After the completion of reaction, the reaction mixture was quenched with saturated ammonium chloride solution (50 mL) then extracted with ethyl acetate (50 mL×2). The combined organic layers were dried over sodium sulphate and concentrated in vacuo to offer the desired product as pure white solid (0.31 g). HPLC/MS (method 1): Rt: 1.621 min; m/z=378 (M+1)+

Step 4: Synthesis of N-[3-(4-formylphenyl)-1H-pyrazol-5-yl]-4-(trifluoromethoxy) benzamide

To a stirred solution of N-[3-[4-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl]-4-(trifluoromethoxy)benzamide (0.2 g) in THF (10 mL) was added Dess Martin periodinane (0.337 g) at ambient temperature and stirred for 3 h. The progress of the reaction was monitored by TLC analysis. After the completion of reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution (50 mL) then extracted with ethyl acetate (50 mL). The organic layer was dried over sodium sulphate and concentrated in vacuo to offer the desired product. The crude product was purified by column chromatography using ethyl acetate and heptane as eluent to offer the desired product as off-white solid (0.15 g). HPLC/MS (method 1): Rt: 1.781 min; m/z=374 (M−1)+

Step 5: Synthesis of N-[3-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-1H-pyrazol-5-yl]-4-(trifluoromethoxy) benzamide (C-57) was achieved following method similar to step 5 of C-1

HPLC/MS (method 1): Rt: 2.016 min; m/z=567 (M+1)+; 1H NMR (500 MHz, DMSO-d6) δ 13.08 (s, 1H), 11.82 (s, 1H), 11.06 (s, 1H), 10.06 (s, 1H), 8.16 (dd, J=6.3, 2.6 Hz, 3H), 8.00 (d, J=8.1 Hz, 2H), 7.82 (d, J=8.1 Hz, 2H), 7.51 (d, J=8.1 Hz, 2H), 7.37 (dd, J=7.7, 1.5 Hz, 1H), 7.31 (ddd, J=7.8, 6.6, 2.1 Hz, 1H), 7.27-7.19 (m, 2H), 7.14 (s, 1H), 3.21-3.07 (m, 1H), 1.20 (d, J=6.9 Hz, 6H).

Example C-58 Synthesis of N-[3-[4-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]-1H-pyrazol-5-yl]-4-(trifluoromethoxy)benzamide (C-58) was achieved following method similar steps of C-2.

HPLC/MS (method 1): Rt: 2.069 min; m/z=607 (M+1)+; 1H NMR (500 MHz, DMSO-d6) δ 13.11 (s, 1H), 11.06 (s, 1H), 8.34 (s, 1H), 8.16 (d, J=8.5 Hz, 2H), 7.86-7.80 (m, 4H), 7.51-7.46 (m, 4H), 7.36-7.28 (m, 2H), 7.15 (s, 1H), 4.20 (q, J=60, 15 Hz, 2H), 2.81-2.79 (m, 1H), 1.18-1.14 (m, 6H).

Example C-60 Synthesis of N-[4-chloro-3-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-1H-pyrazol-5-yl]-4-(trifluoromethoxy)benzamide (C-60)

Step 1: methyl 4-(5-amino-4-chloro-1H-pyrazol-3-yl)benzoate

To a stirred solution of methyl 4-(5-amino-1H-pyrazol-3-yl)benzoate (1.0 g) in dichloroethane (20 mL) was added N-chlorosuccinimide (0.675 g) at ambient temperature and stirred for 3 h. The progress of the reaction was monitored by TLC analysis. After completion of reaction, the reaction mixture was diluted with water (50 mL) then extracted with dichloromethane (50 mL).The organic layer was filtered to remove the insoluble impurities then the filtrate was concentrated in vacuo after drying over sodium sulphate, to afford the product as pale yellow solid (0.872 g).

HPLC/MS (method 1): Rt: 1.493 min; m/z=250 (M−1)+

Step 2: Synthesis of methyl 4-[4-chloro-5-[[4-(trifluoromethoxy)benzoyl]amino]-1H-pyrazol-3-yl]benzoate was achieved following method similar to step 2 of C-1.

HPLC/MS (method 1): Rt: 1.89 min; m/z=438 (M−1)+

Step 3: Synthesis of N-[4-chloro-3-[4-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl]-4-(trifluoromethoxy)benzamide was achieved following method similar to step 3 of C-57.

HPLC/MS (method 1): Rt: 1.664 min; m/z=410 (M−1)+

Step 4: Synthesis of N-[4-chloro-3-(4-formylphenyl)-1H-pyrazol-5-yl]-4-(trifluoromethoxy)benzamide was achieved following method similar to step 4 of C-57.

HPLC/MS (method 1): Rt: 1.813 min; m/z=408 (M−1)+

Step 5: Synthesis of N-[4-chloro-3-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-1H-pyrazol-5-yl]-4-(trifluoromethoxy)benzamide was achieved following method similar to step 5 of C-1.

HPLC/MS (method 1): Rt: 2.325 min; m/z=601 (M+1)+; 1H NMR (500 MHz, DMSO-d6) δ 13.60 (s, 1H), 11.88 (s, 1H), 10.48 (s, 1H), 10.07 (s, 1H), 8.14 (d, J=8.4 Hz, 2H), 8.11-8.04 (m, 2H), 7.88 (d, J=8.1 Hz, 2H), 7.56 (d, J=8.3 Hz, 2H), 7.37 (dd, J=7.8, 1.5 Hz, 1H), 7.31 (td, J=7.8, 7.3, 2.0 Hz, 1H), 7.27-7.16 (m, 3H), 3.14 (p, J=6.8 Hz, 1H), 1.20 (d, J=6.9 Hz, 6H).

Example C-63 Synthesis of N-[5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide (C-62)

Step 1: Synthesis of N-[3-(4-bromophenyl)-1H-1,2,4-triazol-5-yl]-4-(trifluoromethoxy)benzamide

To a stirred solution of 4-(trifluoromethyl)benzoic acid (3.104 g) in DMF (75.0 mL) was added HATU (10.497 g) and DIPEA (6.461 mL) at 0° C. After stirring the reaction mixture for 1 h, 3-(4-bromophenyl)-1H-1,2,4-triazol-5-amine (3.0 g) was added at 0° C. The mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with brine (NaCl aq. Solution) and extracted with EtOAc. The organic phase was dried over sodium sulfate, concentrated under reduced pressure and resultant residue subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and cyclohexane to obtain the title compound as a solid (2.38 g). HPLC/MS (method 2): Rt: 1.359 min; m/z=426.9 (M+1)+

Step 2: Synthesis of N-[5-(4-bromophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide

To a stirred solution of N-[3-(4-bromophenyl)-1H-1,2,4-triazol-5-yl]-4-(trifluoromethoxy)benzamide (1.7 g) in DMF (45.0 mL), sodium hydride (60%, 0.478 g) was added at 0° C. The reaction mixture was stirred 1 h at 0° C. followed by the addition of iodomethane (0.248 mL). After stirring the mixture at room temperature over night, water was added and the mixture was cooled down. The resulting precipitate was filtered and subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and cyclohexane to obtain the title compound as a solid (0.77 g). HPLC/MS (method 2): Rt: 1.230 min; m/z=440.9 (M+1)+.

Step 3: Synthesis of N-[2-methyl-5-[4-[(E)-prop-1-enyl]phenyl]-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide

A solution of N-[5-(4-bromophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy) benzamide (0.77 g), [(E)-prop-1-enyl]boronic acid (0.33 g), potassium carbonate (0.603 g), water (1.5 mL) in 1,2-dimethoxyethane (30 mL) was set under argon atmosphere. Pd(dppf)Cl2 (0.064 g) was added to the reaction mixture and stirred for 48 h at 100° C. The solvent was removed under reduced pressure and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and cyclohexane to obtain the title compound as a solid (0. 520 g). HPLC/MS (method 2): Rt: 1.259 min; m/z=402.9 (M+1)+.

Step 4: Synthesis of N-[5-(4-formylphenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide was achieved following method similar to step 4 of C-1 .

HPLC/MS (method 2): Rt: 1.093 min; m/z=390.8 (M+1)+

Step 5: Synthesis of N-[5-[4-[(E)-[(2-isopropylphenyl)carbamothioylhydrazono]methyl]phenyl]-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide was achieved following method similar to step 5 of C-1.

HPLC/MS (method 2): Rt: 1.303 min; m/z=582.0 (M+1)+. 1H NMR (400 MHz, Chloroform-d) δ 11.08 (s, 1H), 8.98 (s, 1H), 8.14-8.08 (m, 2H), 7.93-7.87 (m, 2H), 7.71 (s, 1H), 7.54 (dd, J=7.5, 1.2 Hz, 1H), 7.45-7.21 (m, 8H), 3.90 (s, 3H), 3.15 (p, J=6.9 Hz, 1H), 1.25 (dd, J=6.9, 2.9 Hz, 6H).

Example C-64

Synthesis of N-[5-[4-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide was achieved following method similar step of C-2.

HPLC/MS (method 2): Rt: 1.331 min; m/z=622.1 (M+1)+. 1H NMR (400 MHz, Chloroform-d) 6 9.57 (s, 1 H), 8.27 (s, 1 H), 8.08 (d, J=7.5 Hz, 2H), 7.98 (d, J=8.1 Hz, 2H), 7.78 (d, J=8.2 Hz, 2H), 7.50-7.45 (m, 2H), 7.33 (dt, J=7.8, 4.4 Hz, 1H), 7.29-7.23 (m, 2H), 7.17 (dt, J=7.8, 1.0 Hz, 1H), 4.01 (d, J=2.9 Hz, 2H), 3.91 (s, 3H), 2.82 (hept, J=6.8 Hz, 1 H), 1.22 (dd, J=6.9, 4.2 Hz, 6H).

Example C-68

Synthesis of N-[2-methyl-5-[4-[(E)-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]oxyiminomethyl]phenyl]-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide was achieved following method similar step of C-32.

HPLC/MS (method 2): Rt: 1.213 min; m/z=594 (M+1)+. 1H NMR (400 MHz, Chloroform-d) δ 8.15 (d, J=7.9 Hz, 3H), 7.95 (d, J=8.0 Hz, 2H), 7.70 (d, J=8.0 Hz, 2H), 7.29 (d, J=7.8 Hz, 2H), 3.93 (s, 3H), 3.58-3.48 (m, 14H), 1.31 (dd, J=6.2, 1.4 Hz, 4H).

TABLE C wherein i-Pr is isopropyl group.           No           Ar—Q

          R¹         HPLC/ MS         Rt min C-1

581 (method 1) 2.16 C-2

621 (method 1) 2.25 C-3

567 (method 1) 2.12 C-4

607 (method 1) 2.16 C-5

580 (method 1) 2.10 C-6

620 (method 1) 2.17 C-7

637 (method 2) 1.28 C-8

609 (method 2) 1.20 C-9

608 (method 1) 1.78 C-10

568 (method 1) 2.25 C-11

608 (method 1) 2.27 C-12

608 (method 1) 2.36 C-13

595 (method 2) 1.34 C-14

635 (method 2) 1.37 C-15

579 (method 2) 1.32 C-16

619 (method 2) 1.35 C-17

619 (method 2) 1.37 C-18

595 (method 1) 2.10 C-19

634 (method 1) 2.08 C-20

634 (method 1) 2.11 C-21

622 (method 1) 1.82 C-22

606 (method 1) 1.96 C-23

596 (method 1) 2.10 C-24

638 (method 1) 2.16 C-25

638 (method 1) 2.19 C-26

611 (method 1) 2.11 C-27

652 (method 1) 2.19 C-28

652 (method 1) 2.20 C-29

593 (method 1) 2.11 C-30

633 (method 1) 2.16 C-31

634 (method 1) 2.21 C-32

605 (method 1) 2.06 C-33

622 (method 1) 1.91 C-34

609 (method 1) 2.14 C-35

649 (method 1) 2.22 C-36

649 (method 1) 2.22 C-37

623 (method 1) 2.21 C-38

663 (method 1) 2.27 C-39

663 (method 1) 2.32 C-40

609 (method 2) 1.11 C-41

637 (method 2) 1.20 C-42

651 (method 2) 1.24 C-43

629 (method 1) 2.14 C-44

670 (method 1) 2.21 C-45

670 (method 1) 2.25 C-46

615 (method 1) 2.06 C-47

621 (method 2) 1.48 C-48

637 (method 2) 1.52 C-49

605 (method 2) 1.47 C-50

607 (method 2) 1.39 C-51

619 (method 2) 1.46 C-52

566 (method 1) 2.10 C-53

608 (method 1) 2.22 C-54

608 (method 1) 2.31 C-55

594 (method 1) 2.03 C-56

624 (method 1) 2.10 C-57

565 (method 1) 2.02 C-58

607 (method 1) 2.06 C-59

607 (method 1) 2.11 C-60

601 (method 1) 2.33 C-61

641 (method 1) 2.04 C-62

641 (method 1) 2.07 C-63

582 (method 2) 1.30 C-64

622 (method 2) 1.34 C-65

622 (method 2) 1.35 C-66

596 (method 2) 1.34 C-67

636 (method 2) 1.37 C-68

594 (method 2) 1.21 C-69

654 (method 1) 2.21 C-70

694 (method 1) 2.33 C-71

694 (method 1) 2.43 C-72

638 (method 1) 2.30 C-73

687 (method 1) 2.08

Biological Example Example B1: Action on Yellow Fever Mosquito (Aedes aegypti)

For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consisted of 96-well-microtiter plates containing 200 μl of tap water per well and 5-15 freshly hatched A. aegypti larvae.

The active compounds or mixtures were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5 μl using a custom built micro atomizer, at two replications.

For experimental mixtures in these tests identical volumes of both mixing partners at the desired concentrations respectively, were mixed together.

After application, microtiter plates were incubated at 28+1° C., 80+5% RH for 2 days. Larval mortality was then visually assessed.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-11, C-12, C-14, C-16, C-17, C-18, C-19, C-20, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-41, C-47, C-48, C-49, C-50, C-51, C-52, C-53, C-54, C-57, C-58, C-59, C-64, C-65, C-66, at 800 ppm showed at least 50% mortality in comparison with untreated controls.

Example B2: Action on Orchid Thrips (Dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1:1 mixture of acetone:water (vol:vol), plus Kinetic® HV at a rate of 0.01% v/v.

Thrips potency of each compound was evaluated by using a floral-immersion technique. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry in Petri dishes. Treated petals were placed into individual re-sealable plastic along with about 20 adult thrips. All test arenas were held under continuous light and a temperature of about 28° C. for duration of the assay. After 3 days, the numbers of live thrips were counted on each petal. The percent mortality was recorded 72 hours after treatment.

In this test, compounds C-1, C-2, C-3, C-5, C-10, C-11, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-23, C-24, C-25, C-27, C-28, C-29, C-30, C-31, C-34, C-35, C-36, C-37, C-38, C-39, C-50, C-52, C-53, C-57, C-58, C-59, C-62, C-63, C-64, C-65, C-66, at 500 ppm showed at least 75% mortality in comparison with untreated controls.

Example B3: Action on Boll Weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96-well-microtiter plates containing an insect diet and 5-10 A. grandis eggs.

The compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μl, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 25+1° C. and about 75+5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-41, C-42, C-50, C-52, C-53, C-54, C-57, C-58, C-59, C-62, C-63, C-64, C-65, C-66, C-67 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

Example B4: Action on Silverleaf Whitefly (Bemisia argentifolii) (Adults)

The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10 ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.

Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and a nontoxic Tygon® tubing connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid. Test plants were maintained in a growth room at about 25° C. and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.

In this test, compounds C-1, C-2, C-10, C-36, C-38, C-39, C-52, C-65, at 300 ppm showed at least 75% mortality in comparison with untreated controls.

Example B5: Action on Tobacco Budworm (Heliothis virescens)

For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 μl, using a custom-built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 28+1° C. and about 80+5% relative humidity for 5 days. Egg and larval mortality were then visually assessed.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-10, C-11, C-12, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-22, C-23, C-24, C-25, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-41, C-42, C-47, C-49, C-50, C-51, C-52, C-53, C-54, C-57, C-58, C-59, C-62, C-63, C-64, C-65, C-66, C-67 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

Example B6: Action on Diamond Back Moth (Plutella xylostella)

The active compound is dissolved at the desired concentration in a mixture of 1:1 (v/v) distilled water: acetone. Surfactant (Kinetic® HV) is added at a rate of 0.01% (v/v). The test solution is prepared at the day of use.

Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dishes lined with moist filter paper and inoculated with ten 3rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0-100%.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-41, C-42, C-47, C-50, C-51, C-52, C-53, C-54, C-55, C-56, C-57, C-58, C-59, C-62, C-63, C-64, C-65, C-66, C-67, at 500 ppm showed at least 75% mortality in comparison with untreated controls.

Example B7: Action on Southern Armyworm (Spodoptera eridania), 2nd Instar Larvae

The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 10 or 20 ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.

Lima bean plants (variety Sieve) were grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 11 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25° C. and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-10, C-1, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-23, C-24, C-25, C-27, C-28, C-29, C-30, C-31, C-32, C-34, C-35, C-36, C-37, C-38, C-39, C-41, C-42, C-43, C-45, C-47, C-51, C-52, C-53, C-54, C-56, C-62, C-64, C-65, C-66 at 300 ppm showed at least 75% mortality in comparison with untreated controls. 

1. A compound of formula I

wherein A is N or CR^(A); B¹ is N or CR^(B1); B² is N or CR^(B2); B³ is N or CR^(B3); B⁴ is N or CR^(B4); W is O, S(═O)_(m), or NR⁶; R^(A) is H, halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy, phenylcarbonyl, phenylthio, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R^(B1), R^(B2), R^(B3), and R^(B4) independently of each other are H, halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy, phenylcarbonyl, phenylthio, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); Q is —C(R⁴R⁵)—O—, —C(═O)—O—, —S(═O)_(m)—C(R⁷R⁸)—, —N(R²)—S(═O)_(m)—, —N(R²)—C(R⁹R¹⁰)—, —C(═O)—C(R¹⁹R²⁰)—, —N(R²)—C(═O)—, —N(R²)—C(═S)—, —C(R¹³R¹⁴)—C(R¹⁵R¹⁶)—, —N═C(X)—, or —N(R²)—C(═NR)—; wherein Ar is bound to either side of Q; m is 0, 1, or 2; X is H, halogen, SR⁷, OR⁸, or N(R³)₂; R is H, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, or C₃-C₆-cycloalkyl, wherein the alkyl, alkenyl, and cycloalkyl moieties are unsubstituted or substituted with halogen, OR⁸, N(R³)₂; R³ is H, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl; R² is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁹, R²⁰ are, identical or different, H, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R⁶ is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, —CH₂—C(═O)—OR^(a), or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or substituted with R^(Ar), wherein R^(Ar) is halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy, phenylcarbonyl, phenylthio or —CH₂-phenyl, wherein phenyl rings are unsubstituted or substituted with R^(f); R¹ is a moiety of formula Y—Z-T-R¹¹ or Y—Z-T-R¹²; wherein Y is —CR^(ya)═N—, wherein the N is bound to Z; —NR^(yc)—C(═O)—, wherein C(═O) is bound to Z; or —NR^(yc)—C(═S)—, wherein C(═S) is bound to Z; Z is a single bond; —NR^(zc)—C(═O)—, wherein C(═O) is bound to T; —NR^(zc)—C(═S)—, wherein C(═S) is bound to T; —N═C(S—R^(za))—, wherein T is bound to the carbon atom; —O—C(═O)—, wherein T is bound to the carbon atom; or —NR^(zc)—C(S—R^(za))═, wherein T is bound to the carbon atom; wherein if Y is other than —CR^(ya)═N—, Z is other than —N═C(S—R^(za))—; T is O, N or N—R^(T); R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), aryl, aryl-carbonyl, aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl, hetaryl, carbonyl-hetaryl, hetaryl-C₁-C₄-alkyl or hetaryloxy-C₁-C₄-alkyl, wherein the phenyl rings are unsubstituted or substituted with R^(g) and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl; R¹² is a radical of the formula A¹;

wherein # indicates the point of attachment to T; R¹²¹, R¹²², R¹²³ are, identical or different, H, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonlyoxy, C₁-C₆-alkenylcarbonlyoxy, C₃-C₆-cycloalkylcarbonlyoxy, wherein the alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and cycloalkyl moieties are unsubstituted or substituted with halogen, or NR^(b)R^(c), or one of R¹²¹, R¹²², R¹²³ may also be oxo; R¹²⁴ is H, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy, or C₂-C₆-alkenyloxy, wherein the alkyl, alkoxy, alkenyl and alkenyloxy moieties are unsubstituted or substituted with halogen; and where R^(ya) is H, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R^(yc), R^(zc) are, identical or different, H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl, or C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen; R^(T) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R^(zc) together with R^(T) if present, may form C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂ moieties may be replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h); R^(za) is H, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, C₁-C₄-alkyl-C₃-C₆-cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, phenylcarbonyl, or CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R^(za) together with R^(T) if present, may form C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂ moieties may be replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h); R^(a), R^(b) and R^(c) are, identical or different, H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C₁-C₆-alkylene-CN, phenyl, or CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R^(d) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, phenyl, or CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R^(e) is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen, phenyl and —CH₂-phenyl, wherein the phenyl rings are unsubstituted or substituted with R^(f); R^(f) is halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxyx-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e); R^(g) is halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e); R^(h) is halogen, OH, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, or CN; except the compound tert-Butyl N-[4-(5-[3-(aminocarbonyl)-2,4-difluorophenoxy]methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamate; and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
 2. The compound of formula I according to claim 1, wherein W is NR⁶, A is CR^(A), B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4).
 3. The compound of formula I according to claim 1, wherein W is O, A is N, B¹ is CR^(B1), B² is CR^(B2), B³ is CR^(B3), and B⁴ is CR^(B4).
 4. The compound of formula I according to claim 1, wherein W is S(═O)_(m), A is CR^(A), B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4).
 5. The compound of formula I according to claim 1, wherein W is NR⁶, A is CR^(A), B¹ is CR^(B1), B² is N, B³ is CR^(B3), and B⁴ is CR^(B4).
 6. The compound of formula I according to claim 1, wherein W is NR⁶, A is CR^(A), B¹ is CR^(B1), B² is N, B³ is N, and B⁴ is CR^(B4).
 7. The compound of formula I according to claim 1, wherein W is S(═O)_(m), A is N, B¹ is N, B² is CR^(B2), B³ is CR^(B3), B⁴ is CR^(B4).
 8. The compound of formula I according to claim 1, wherein R¹ are formulas YZT-1 to YZT-9, wherein

denotes attachment to the 6 membered ring;

wherein R¹¹, R¹², R^(T), R^(ya), R^(yc), R^(za) and R^(zc) are as defined in claim
 1. 9. The compound of formula I according to claim 1, wherein Ar are formulas Ar-1 to Ar-22


10. A composition comprising at least one compound of formula I according to claim 1, an N-oxide or an agriculturally acceptable salt thereof, and a further active substance.
 11. A method for combating or controlling invertebrate pests, comprising contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound according to claim
 1. 12. A method for protecting growing plants from attack or infestation by invertebrate pests, comprising contacting a plant, or soil or water wherein the plant is growing, with a pesticidally effective amount of at least one compound according to claim
 1. 13. A seed comprising a compound according to claim 1, or the enantiomers, diastereomers or salts thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
 14. (canceled)
 15. A method for treating or protecting an animal from infestation or infection by invertebrate pests comprising contacting the animal with a pesticidally effective amount of at least one compound of the formula I according to claim 1, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof. 